Leucine, N-carboxy-, N-benzyl ester, L- → HCID 86608592, compound

HRID 2111532Notes

Reaction equation

HRID 2111532 reaction equation
[NH:1]([C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])[C@H:2]([C:7](O)=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].Cl.[C:21]1([CH:27]([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)[C@H:28]([NH2:51])[CH:29]=[CH:30][S:31]([CH:34]=[CH:35][C@@H:36]([NH2:50])[CH:37]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)(=[O:33])=[O:32])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[C:52]1([CH:27]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C@H:28]([NH:51][C:7](=[O:8])[C@H:2]([CH2:3][CH:4]([CH3:6])[CH3:5])[NH:1][C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH:29]=[CH:30][S:31]([CH:34]=[CH:35][C@@H:36]([NH:50][C:7](=[O:8])[C@H:2]([CH2:3][CH:4]([CH3:5])[CH3:6])[NH:1][C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH:37]([C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)(=[O:33])=[O:32])[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=1

Participants

3

Reactant 2

HCID 74840Leucine, N-carboxy-, N-benzyl ester, L-HCID 131727420Phenyl-(3S)-3-amino-4-phenylbut-1-enyl Sulfone Hydrochloride

Product 1

HCID 86608592HCID 86608592, compoundYield 82%

Procedure

Cbz-Leu-Phe-VS-Ph was prepared from Cbz-Leu-OH and Phe-VS-Ph.HCl using standard mixed anhydride coupling method, yield 82%. 1H-NMR (CDCl3) δ 0.8-0.9 (2d, 6H, 2×Leu-CH3), 1.4-1.6 (m, 2H, Leu-CH2), 2.06 (m, 1H, Leu-CH), 2.9-3.0 (m, 2H, CH2-Phe), 3.9-4.0 (m, 1H, α-H), 4.8-4.9 (b, 1H, NH), 4.9-5.0 (m, 1H, α-H), 5.1 (m, 2H, Cbz) 6.3-6.4 (d & b, 2H, NH and CH═), 6.9-7.0 (dd, 1H, CH═), 7.1-7.4 (m, 10H, 2×Ph), 7.5-7.7 (m, 5H, SO2-Ph). MS (ESI) m/z 535.

Sources & evidence

ORD record
ord-1007673c1de4409c9e86f98e7f9d69c4
Source dataset
uspto-grants-2009_04
Patent number
US07521427B2

Reaction notes

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