Sodium borohydride → HCID 54510319, compound

HRID 24655Notes

Reaction equation

HRID 24655 reaction equation
[BH4-].[Na+].[CH2:3]([O:5][C:6](=[O:37])[C@H:7]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[O:32][CH3:33])=[C:22]([C:34](=[O:36])[CH3:35])[CH:21]=1)[NH:8][C:9](=[O:18])[C:10]1[C:15]([Cl:16])=[CH:14][CH:13]=[CH:12][C:11]=1[Cl:17])[CH3:4]>CO>[CH2:3]([O:5][C:6](=[O:37])[C@H:7]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[O:32][CH3:33])=[C:22]([CH:34]([OH:36])[CH3:35])[CH:21]=1)[NH:8][C:9](=[O:18])[C:10]1[C:15]([Cl:16])=[CH:14][CH:13]=[CH:12][C:11]=1[Cl:17])[CH3:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 541927443-acety-1N-(2,6-dichlorobenzoyl)-4-(2-methoxyphenyl)-L-phenylalanine ethyl ester

Product 1

HCID 54510319HCID 54510319, compoundYield 44.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

NaBH4 (12 mg) was added to a solution of 3-acetyl-N-(2,6-dichlorobenzoyl)-4-(2-methoxyphenyl)-L-phenylalanine ethyl ester (0.1 g) in MeOH (3 mL) and the mixture was stirred at room temperature for 2 h. The mixture was quenched with 1 N HCl and extracted with CH2Cl2. The extract was washed successively with 1 N HCl and brine, dried and evaporated. The residue was purified by a flash column chromatography (silica gel; eluent: hexanes/EtOAc 3:1) to yield 45 mg of N-(2,6-dichlorobenzoyl)-3-(1-hydroxyethyl)-4-(2-methoxyphenyl)-L-phenylalanine ethyl ester. ESMS: m/z 516 (MH+).

Workup

  1. customThe mixture was quenched with 1 N HCl
  2. extractionextracted with CH2Cl2
  3. washThe extract was washed successively with 1 N HCl and brine
  4. customdried
  5. customevaporated
  6. customThe residue was purified by a flash column chromatography (silica gel; eluent: hexanes/EtOAc 3:1)

Sources & evidence

ORD record
ord-5a13e8715cb2484bbda686ebc97396b8
Source dataset
uspto-grants-2005_02
Patent number
US06855843B2

Reaction notes

Loading…