4-(Propan-2-yl)benzene-1-sulfonyl chloride → 3-(4-Benzyloxy-phenyl)-2(S)-[2(S)-(4-isopropyl-benzenesulfonylamino)-4-methyl-pentanoylamino]-propionic acid tert-butyl ester

HRID 2230318Notes

Reaction equation

HRID 2230318 reaction equation
[C:1]([O:5][C:6](=[O:32])[CH:7]([NH:23][C:24](=[O:31])[CH:25]([NH2:30])[CH2:26][CH:27]([CH3:29])[CH3:28])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[CH:33]([C:36]1[CH:41]=[CH:40][C:39]([S:42](Cl)(=[O:44])=[O:43])=[CH:38][CH:37]=1)([CH3:35])[CH3:34]>>[C:1]([O:5][C:6](=[O:32])[C@@H:7]([NH:23][C:24](=[O:31])[C@@H:25]([NH:30][S:42]([C:39]1[CH:40]=[CH:41][C:36]([CH:33]([CH3:35])[CH3:34])=[CH:37][CH:38]=1)(=[O:44])=[O:43])[CH2:26][CH:27]([CH3:28])[CH3:29])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:11][CH:10]=1)([CH3:3])([CH3:2])[CH3:4]

Participants

3

Reactant 2

HCID 27348824-(Propan-2-yl)benzene-1-sulfonyl chlorideHCID 540817292-(2-Amino-4-methyl-pentanoylamino)-3-(4-benzyloxy-phenyl)-propionic acid tert-butyl ester

Product 1

HCID 700610563-(4-Benzyloxy-phenyl)-2(S)-[2(S)-(4-isopropyl-benzenesulfonylamino)-4-methyl-pentanoylamino]-propionic acid tert-butyl esterYield 71%

Procedure

Using a procedure similar to that described in Example 36, the product from Example AI ([S-(R*,R*)]-2-{2-amino-4-methyl-pentanoylamino}-3-(4-benzyloxy-phenyl)-propionic acid tert-butyl ester) (0.20 g, 0.45 mmol) and 4-isopropylphenylsulfonyl chloride (0.10 g, 0.45 mmol) were coupled to give the title compound as a white solid (0.20 g, 71%), mp=147-148° C.

Sources & evidence

ORD record
ord-ef8b567bb3cc4fc291fff7d7d96a7410
Source dataset
uspto-grants-2002_07
Patent number
US06423689B1

Reaction notes

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