Sodium borohydride → N-(2,6-dichlorobenzoyl)-4-[2-(hydroxymethyl)phenyl]-L-phenylalanine methyl ester

HRID 24647Notes

Reaction equation

HRID 24647 reaction equation
[BH4-].[Na+].[CH3:3][O:4][C:5](=[O:33])[C@H:6]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[CH:31]=[O:32])=[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]>CO>[CH3:3][O:4][C:5](=[O:33])[C@H:6]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[CH2:31][OH:32])=[CH:21][CH:20]=1)[NH:7][C:8](=[O:17])[C:9]1[C:10]([Cl:16])=[CH:11][CH:12]=[CH:13][C:14]=1[Cl:15]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 54369932N-(2,6-Dichlorobenzoyl)-4-(2-formylphenyl)-L-phenylalanine methyl ester

Product 1

HCID 53694008N-(2,6-dichlorobenzoyl)-4-[2-(hydroxymethyl)phenyl]-L-phenylalanine methyl esterYield 103.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

NaBH4 (21 mg) was added to a solution of N-(2,6-dichlorobenzoyl)-4-(2-formylphenyl)-L-phenylalanine methyl ester (0.23 g) in MeOH (5 mL) and the mixture was stirred at room temperature for 3 h. The reaction was quenched with acetone and the mixture was evaporated. The residue was partitioned between EtOAc and water. The EtOAc layer was dried (MgSO4) and evaporated to yield N-(2,6-dichlorobenzoyl)-4-[2-(hydroxymethyl)phenyl]-L-phenylalanine methyl ester (0.24 g). ESMS: m/z 480 ([M+Na]+).

Workup

  1. customThe reaction was quenched with acetone
  2. customthe mixture was evaporated
  3. customThe residue was partitioned between EtOAc and water
  4. dry with materialThe EtOAc layer was dried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-75ae478bd80e476b9173572378913963
Source dataset
uspto-grants-2005_02
Patent number
US06855843B2

Reaction notes

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