(2S)-2-(((tert-butoxy)carbonyl)amino)-2-phenylacetic acid → (3aS,4S,7aS)-7,7-diphenyl-4-(2-methoxyphenyl)-2-[(S)-2-tert-butoxycarbonylamino-2-phenylacetyl]perhydroisoindol-4-ol

HRID 375429Notes

Reaction equation

HRID 375429 reaction equation
Cl.[C:2]1([C:8]2([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C@@H:16]3[C@@H:12]([CH2:13][NH:14][CH2:15]3)[C@@:11]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[O:24][CH3:25])([OH:17])[CH2:10][CH2:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:32]([O:36][C:37]([NH:39][C@@H:40]([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[C:41](O)=[O:42])=[O:38])([CH3:35])([CH3:34])[CH3:33]>>[C:26]1([C:8]2([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C@@H:16]3[C@@H:12]([CH2:13][N:14]([C:41](=[O:42])[C@@H:40]([NH:39][C:37]([O:36][C:32]([CH3:34])([CH3:33])[CH3:35])=[O:38])[C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)[CH2:15]3)[C@@:11]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[O:24][CH3:25])([OH:17])[CH2:10][CH2:9]2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

3

Reactant 2

HCID 11010409(2S)-2-(((tert-butoxy)carbonyl)amino)-2-phenylacetic acidHCID 70218598(3aS,4S,7aS)-7,7-diphenyl-4-(2-methoxyphenyl)perhydroisoindol-4-ol hydrochloride

Product 1

HCID 22857047(3aS,4S,7aS)-7,7-diphenyl-4-(2-methoxyphenyl)-2-[(S)-2-tert-butoxycarbonylamino-2-phenylacetyl]perhydroisoindol-4-olYield 11.1%

Procedure

By working in accordance with Example 4, starting from 2.25 g of (3aS,4S,7aS)-7,7-diphenyl-4-(2-methoxyphenyl)perhydroisoindol-4-ol hydrochloride and 1.25 g of (S)-2-tert-butoxycarbonylamino-2-phenylacetic acid, 0.35 g of (3aS,4S,7aS)-7,7-diphenyl-4-(2-methoxyphenyl)-2-[(S)-2-tert-butoxycarbonylamino-2-phenylacetyl]perhydroisoindol-4-ol is obtained in the form of a white foam.

Sources & evidence

ORD record
ord-4ecacaa7884848b982d7ee11b68b7b85
Source dataset
uspto-grants-1996_01
Patent number
US05484804

Reaction notes

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