D-Tryptophan benzyl ester → (R)-alpha-[(3-t-Butoxycarbonylamino-3-methyl-1-oxobutyl)amino]-1-H-indole-3-propanoic acid benzyl ester

HRID 1920

Reaction equation

HRID 1920 reaction equation
[CH2:1]([O:8][C:9](=[O:22])[C@@H:10]([CH2:12][C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[NH:15][CH:14]=1)[NH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23]([O:27][C:28]([NH:30][C:31]([CH3:37])([CH3:36])[CH2:32][C:33](O)=[O:34])=[O:29])([CH3:26])([CH3:25])[CH3:24]>>[CH2:1]([O:8][C:9](=[O:22])[C@H:10]([NH:11][C:33](=[O:34])[CH2:32][C:31]([NH:30][C:28]([O:27][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:29])([CH3:37])[CH3:36])[CH2:12][C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[NH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 6995075D-Tryptophan benzyl esterHCID 103760463-((tert-Butoxycarbonyl)amino)-3-methylbutanoic acid

Product 1

HCID 86752263(R)-alpha-[(3-t-Butoxycarbonylamino-3-methyl-1-oxobutyl)amino]-1-H-indole-3-propanoic acid benzyl ester

Procedure

Prepared from D-tryptophan benzyl ester (1 g; 3.40 mmol) and 3-t-butoxycarbonylamino-3-methylbutanoic acid (0.91 g; 4.19 mmol) by the procedure described in Example 6, Step C. The yield was 0.981 g (58%).

Sources & evidence

ORD record
ord-e392efa1dd0c43839d8e3026d6f4b2ee
Source dataset
uspto-grants-1998_03
Patent number
US05726319

Linked notes

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