References and Notes
1
Ghose AK.
Viswanadhan VN.
Wendoloski JJ.
J. Comb. Chem.
1999,
1:
55
2
Montalbetti CAGN.
Falque V.
Tetrahedron
2005,
61:
10827
3
Pearson AJ.
Roush WR.
Handbook of Reagents for Organic Synthesis: Activating Agents and Protecting Groups
Wiley;
New York:
1999.
p.370-373
4
Chu W.
Tu Z.
McElveen E.
Xu J.
Taylor M.
Luedtke RR.
Mach RH.
Bioorg. Med. Chem.
2005,
13:
77
5
Klosa J.
J. Prakt. Chem. (Leipzig)
1962,
19:
45
6
Rayle HL.
Fellmeth L.
Org. Process Res. Dev.
1999,
3:
172
7
Venkataraman K.
Wagle DR.
Tetrahedron Lett.
1979,
32:
3037
8
Klausner Y.
Bodansky M.
Synthesis
1974,
549
9
Shioiri T.
Ninomiya K.
Yamada SY.
J. Am. Chem. Soc.
1972,
94:
6203
10
Paul R.
Anderson W.
J. Am. Chem. Soc.
1960,
82:
4596
11
Dale DJ.
Draper J.
Dunn PJ.
Hughes ML.
Hussain F.
Levett PC.
Ward GB.
Wood AS.
Org. Process Res. Dev.
2002,
6:
767
12
Wittenberger SJ.
McLaughlin MA.
Tetrahedron Lett.
1999,
40:
7175
13
Chu W.
Tu Z.
McElveen E.
Xu J.
Taylor M.
Luedtke RR.
Mach RH.
Bioorg. Med. Chem.
2005,
13:
77
14
Mikolajczyk M.
Kielbasinski P.
Tetrahedron
1981,
37:
233
15
Fuller WD.
Cohen MP.
Shabankareh M.
Blair RK.
J. Am. Chem. Soc.
1990,
112:
7414
16
Ishihara K.
Ohara S.
Yamamoto H.
J. Org. Chem.
1996,
61:
4196
17
Ishihara K.
Ohara S.
Yamamoto H.
Macromolecules
2000,
33:
3511
18
Gangwar GM.
Pauletti T.
Siahaan J.
Stella VJ.
Borchardt RT.
J. Org. Chem.
1997,
62:
1356
19
Jaoudai M.
Martinez J.
Castro B.
Barcelo G.
Sennyey G.
Senet J.-P.
J. Org. Chem.
1987,
52:
2364
20
Wang W.
McMurray JS.
Tetrahedron Lett.
1999,
40:
2501
21
Kunishima M.
Kawachi C.
Iwasaki F.
Terao K.
Tani S.
Tetrahedron Lett.
1999,
40:
5327
22a
Dawson PE.
Muir TW.
Clark-Lewis I.
Kent SB.
Science
1994,
266:
776
22b
Dawson PE.
Churchill MJ.
Ghadiri MR.
Kent SB.
J. Am. Chem. Soc.
1997,
119:
4325
22c
Dawson PE.
Kent SB.
Annu. Rev. Biochem.
2000,
69:
923
23a
Köhn M.
Breinbauer R.
Angew. Chem. Int. Ed.
2004,
43:
3106
23b
Fiona L.
Lin FL.
Hoyt HT.
Halbeek H.
Bergman RG.
Bertozzi CR.
J. Am. Chem. Soc.
2005,
127:
2686
23c
Soellner MB.
Tam A.
Raines RT.
J. Org. Chem.
2006,
71:
9824
24a
Carrillo N.
Davalos EA.
Russak JA.
Bode JW.
J. Am. Chem. Soc.
2006,
128:
1452
24b
Bode JW.
Fox RM.
Baucom KD.
Angew. Chem. Int. Ed.
2006,
45:
1248
25
Somlai C.
Szokan G.
Balaspiri L.
Synthesis
1992,
285
26
Shendage DM.
Fröhlich R.
Haufe G.
Org. Lett.
2004,
6:
3675
27
General Experimental Procedure.
To a solution of α-amino acid 1a-e (1.73 mmol) in H2O (4 mL), CDI (2.08 mmol) was added at ambient temperature and the reaction mixture was stirred for 30 min. Aliphatic or aromatic amine 2a-f (2.08 mmol) was then added and the stirring continued for another 7.5-23.5 h at ambient temperature. The solvent was evaporated under reduced pressure to afford crude product. Column chromatographic purification of crude product on basic alumina using CHCl3-MeOH as eluent produced amides 3a-m in 27-73% yield.
28
Analytical Data of N
1-Benzyl-(2
S
)-2-amino-5-amino(imino)methylaminopentanamide (
3a)
Yield 73%; white solid; mp 176-178 °C. MS (APCI): 264.1 [M + 1]+. 1H NMR (300 MHz, D2O): δ = 1.61 (m, 2 H), 1.89 (m, 2 H), 3.16 (t, 2 H, J = 7.3 Hz), 3.69 (t, 1 H, J = 6.8 Hz), 4.39 (s, 2 H), 7.23-7.29 (m, 5 H). 13C NMR (75 MHz, D2O): δ = 25.53, 30.14, 41.47, 43.59, 54.88, 127.70, 128.15, 128.90, 139.14, 158.44, 175.21. IR (KBr): 3445, 3326, 3033, 2923, 2872, 1685, 1573, 1458 cm-1. Anal. Calcd for C13H21N5O: C, 59.32; H, 7.98; N, 26.62. Found: C, 59.24; H, 7.93; N, 26.58.
29
Analytical Data of N
1-(3-Quinolyl)-(2
S
)-2-amino-5-amino(imino)methylaminopentanamide (
3f).
Yield 50%; yellow solid; mp 217-219 °C. MS (APCI): 301.1 [M + 1]+. 1H NMR (300 MHz, D2O): δ = 1.66 (m, 2 H), 1.83 (m, 2 H), 3.09 (t, 2 H, J = 7.1 Hz), 3.69 (t, 1 H, J = 6.4 Hz), 7.25 (m, 1 H), 7.61 (m, 2 H), 7.79 (m, 1 H), 7.87 (m, 1 H), 8.55 (m, 1 H). 13C NMR (75 MHz, D2O): δ = 25.14, 31.97, 41.25, 55.90, 118.21, 127.03, 127.69, 127.92, 137.50, 143.95, 157.34, 173.46. IR (KBr): 3414, 3293, 3019, 2912, 2849, 1679, 1552, 1470, 1386 cm-1. Anal. Calcd for C15H20N6O: C, 60.00; H, 6.67; N, 28.00. Found: C, 59.96; H, 6.65; N, 27.95.
30
Analytical Data of N
1-Benzyl-(2
S
)-2-amino-3-(1
H
-4-imidazolyl)propanamide (
3g).
Yield 60%; white solid; mp 193-195 °C. MS (APCI): 245.2 [M + 1]+. 1H NMR (300 MHz, D2O): δ = 3.26 (d, 2 H, J = 7.2 Hz), 4.08 (t, 1 H, J = 7.2 Hz), 4.36 (s, 2 H), 6.85 (s, 1 H), 7.18-7.22 (m, 5 H), 7.48 (s, 1 H). 13C NMR (75 MHz, D2O): δ = 33.81, 46.73, 58.87, 122.15, 126.95, 127.07, 127.38, 128.15, 128.46, 133.90, 134.78, 143.56, 176.41. IR (KBr): 3458, 3331, 3046, 2948, 2883, 1692, 1638, 1573, 1535, 1370 cm-1. Anal. Calcd for C13H16N4O: C, 63.93; H, 6.56; N, 22.95. Found: C, 63.88; H, 6.52; N, 22.90.
31
Analytical Data of N
1-Methyl-(2
S
)-2-amino-3-(1
H
-4-imidazolyl)propanamide (
3h).
Yield 56%; off-white solid; mp 127-128 °C. MS (APCI): 169.2 [M + 1]+. 1H NMR (300 MHz, D2O): δ = 2.77 (s, 3 H), 3.38 (d, 2 H, J = 7.2 Hz), 4.18 (t, 1 H, J = 7.2 Hz), 6.91 (s, 1 H), 7.59 (s, 1 H). 13C NMR (75 MHz, D2O): δ = 28.13, 36.58, 55.11, 117.74, 131.43, 136.37, 174.72. IR (KBr): 3421, 3305, 2960, 2893, 1694, 1638, 1584, 1541 cm-1. Anal. Calcd for C7H12N4O: C, 50.00; H, 7.14; N, 33.33. Found: C, 49.94; H, 7.09; N, 33.30.
32
Analytical Data of N
1-Benzyl-2-aminoacetamide (
3m).
Yield 52%; off-white solid; mp 142-144 °C. MS (APCI): 165.3 [M + 1]+. 1H NMR (300 MHz, D2O): δ = 3.67 (s, 2 H), 4.41 (s, 2 H), 7.14-7.19 (m, 5 H). 13C NMR (75 MHz, D2O): δ = 42.57, 49.60, 126.33, 127.17, 128.41, 143.89, 173.70. IR (KBr): 3454, 3319, 2971, 2888, 1687, 1578, 1453 cm-1. Anal. Calcd for C9H12N2O: C, 65.85; H, 7.32; N, 17.07. Found: C, 65.78; H, 7.26; N, 16.99.
33 The optical purity of amide analogues was assessed on HPLC using CHIRALPAK WH chiral column (ID 0.46 cm, particle size 10 µm), and results indicate presence of ≤1.0% of the d-enantiomer in all cases.
34
Staab HA.
Justus Liebigs Ann. Chem.
1957,
609:
75
35
Staab HA.
Lueking M.
Duerr FH.
Chem. Ber.
1962,
95:
1275
36
Klijn JE.
Engberts JBFN.
Nature (London)
2005,
435:
746
