N-Carbobenzoxy-L-valine → HCID 86608595, compound

HRID 2111538Notes

Reaction equation

HRID 2111538 reaction equation
[NH:1]([C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])[C@H:2]([C:6](O)=[O:7])[CH:3]([CH3:5])[CH3:4].Cl.[C:20]1([CH:26]([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[C@H:27]([NH2:50])[CH:28]=[CH:29][S:30]([CH:33]=[CH:34][C@@H:35]([NH2:49])[CH:36]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)(=[O:32])=[O:31])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[C:51]1([CH:26]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C@H:27]([NH:50][C:6](=[O:7])[C@H:2]([CH:3]([CH3:5])[CH3:4])[NH:1][C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH:28]=[CH:29][S:30]([CH:33]=[CH:34][C@@H:35]([NH:49][C:6](=[O:7])[C@H:2]([CH:3]([CH3:4])[CH3:5])[NH:1][C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH:36]([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)(=[O:32])=[O:31])[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=1

Participants

3

Reactant 2

HCID 726987N-Carbobenzoxy-L-valineHCID 131727420Phenyl-(3S)-3-amino-4-phenylbut-1-enyl Sulfone Hydrochloride

Product 1

HCID 86608595HCID 86608595, compoundYield 98%

Procedure

Cbz-Val-Phe-VS-Ph was prepared from Cbz-Val-OH and Phe-VS-Ph.HCl using standard mixed anhydride coupling method, yield 98%. 1H-NMR (CDCl3) δ 0.70-0.84 (2d, 6H, Val-CH3), 2.06 (m, 1H, Val-CH), 2.91 (m, 2H, CH2-Phe), 3.82 (m, 1H, α-H), 4.80-4.90 (m, 1H, α-H), 5.10 (s, 2H, Cbz), 5.96 (d, 1H, NH) 6.34 (d, 1H, 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 521 (M+1, 100%).

Sources & evidence

ORD record
ord-0cb81bfaad6f4592830e425f8308e032
Source dataset
uspto-grants-2009_04
Patent number
US07521427B2

Reaction notes

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