Boc-L-3,3-Diphenylalanine → (1S,5S)-(1-{5-[(3-Amino-4-fluoro-benzenesulfonyl)-isobutyl-amino]-6-hydroxy-hexylcarbamoyl}-2,2-diphenyl-ethyl)-carbamic Acid tert-Butyl Ester

HRID 987995Notes

Reaction equation

HRID 987995 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([N:9]([CH2:21][CH:22]([CH3:24])[CH3:23])[S:10]([C:13]1[CH:18]=[CH:17][C:16]([F:19])=[C:15]([NH2:20])[CH:14]=1)(=[O:12])=[O:11])[CH2:7][OH:8].[C:25]([O:29][C:30]([NH:32][C@@H:33]([CH:37]([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:34](O)=[O:35])=[O:31])([CH3:28])([CH3:27])[CH3:26]>>[C:25]([O:29][C:30](=[O:31])[NH:32][C@H:33]([C:34](=[O:35])[NH:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([N:9]([S:10]([C:13]1[CH:18]=[CH:17][C:16]([F:19])=[C:15]([NH2:20])[CH:14]=1)(=[O:12])=[O:11])[CH2:21][CH:22]([CH3:24])[CH3:23])[CH2:7][OH:8])[CH:37]([C:44]1[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1)[C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)([CH3:26])([CH3:28])[CH3:27]

Participants

3

Reactant 2

HCID 2761487Boc-L-3,3-DiphenylalanineHCID 67531641(1S)-N-(5-amino-1-hydroxymethyl-pentyl)-N-isobutyl-3-amino-4-fluoro-benzenesulfonamide

Product 1

HCID 67531855(1S,5S)-(1-{5-[(3-Amino-4-fluoro-benzenesulfonyl)-isobutyl-amino]-6-hydroxy-hexylcarbamoyl}-2,2-diphenyl-ethyl)-carbamic Acid tert-Butyl EsterYield 46%

Procedure

The title compound was prepared from the crude amine mixture of (1S)-N-(5-amino-1-hydroxymethyl-pentyl)-N-isobutyl-3-amino-4-fluoro-benzenesulfonamide which is described earlier (example 53, step C) and (2S)-2-tert-butoxycarbonylamino-3,3-diphenyl-propionic acid using general procedure A. The crude residue was purified by semi-preparative HPLC in several batches of 80 mg using a gradient of 50 to 80% of acetonitrile over 30 min and a flow rate of 15 mL/min, retention time=20.2 min. All the pure fractions were combined to provide 630 mg (46% yield) of the title compound.

Workup

  1. customThe crude residue was purified by semi-preparative HPLC in several batches of 80 mg
  2. customover 30 min

Sources & evidence

ORD record
ord-384460e99a2c4d78a5b64999ea45a32c
Source dataset
uspto-grants-2003_10
Patent number
US06632816B1

Reaction notes

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