Sodium borohydride → N-(2,6-Dichlorobenzoyl)-4-(2-hydroxymethyl-3-thienyl)-L-phenylalanine

HRID 24672Notes

Reaction equation

HRID 24672 reaction equation
[BH4-].[Na+].C[O:4][C:5](=[O:32])[C@H:6]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:29]=[CH:28][S:27][C:26]=2[CH:30]=[O:31])=[CH:21][CH:20]=1)[NH:7][C:8](=[O:17])[C:9]1[C:14]([Cl:15])=[CH:13][CH:12]=[CH:11][C:10]=1[Cl:16]>>[Cl:16][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]([Cl:15])[C:9]=1[C:8]([NH:7][C@H:6]([C:5]([OH:32])=[O:4])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:29]=[CH:28][S:27][C:26]=2[CH2:30][OH:31])=[CH:21][CH:20]=1)=[O:17]

Participants

3

Reactant 2

HCID 4311764Sodium borohydrideHCID 54164979N-(2,6-Dichlorobenzoyl)-4-(2-formyl-3-thienyl)-L-phenylalanine methyl ester

Product 1

HCID 53842613N-(2,6-Dichlorobenzoyl)-4-(2-hydroxymethyl-3-thienyl)-L-phenylalanine

Procedure

The title compound was prepared by NaBH4 reduction of N-(2,6-Dichlorobenzoyl)-4-(2-formyl-3-thienyl)-L-phenylalanine methyl ester followed by hydrolysis as described in Example 50. ESMS m/z 472 (M+-Na), 448 (M−H)−.

Workup

  1. customfollowed by hydrolysis

Sources & evidence

ORD record
ord-f592717be8624264858e7cf42d0095f4
Source dataset
uspto-grants-2005_02
Patent number
US06855843B2

Reaction notes

Loading…