Sodium borohydride → Methyl 2-acetamido-3-hydroxy-3-(4-methoxyphenyl)propanoate

HRID 58871Notes

Reaction equation

HRID 58871 reaction equation
[C:1]([NH:4][CH:5]([C:10]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)=[O:11])[C:6]([O:8][CH3:9])=[O:7])(=[O:3])[CH3:2].[BH4-].[Na+]>CO>[C:1]([NH:4][CH:5]([CH:10]([OH:11])[C:12]1[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=1)[C:6]([O:8][CH3:9])=[O:7])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 670181992-Acetylamino-3-(4-methoxy-phenyl)-3-oxo-propionic acid methyl ester

Product 1

HCID 84582340Methyl 2-acetamido-3-hydroxy-3-(4-methoxyphenyl)propanoateYield 59%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of methyl 2-acetamido-3-(4-methoxyphenyl)-3-oxopropanoate (22.7 g, 85.7 mmol) in methanol (500 mL) was cooled to 0° C. and NaBH4 (976 mg, 25.7 mmol) was added in portions. The reaction mixture was stirred for 1 h at 0° C. and then quenched with water (1 L). The resulting mixture was extracted with EtOAc (300 ml×3). The organic extracts were combined, dried over anhydrous sodium sulfate and concentrated. The residue was washed with petroleum ether/EtOAc (100 mL, 10:1) to afford methyl 2-acetamido-3-hydroxy-3-(4-methoxyphenyl)propanoate (13.5 g, 59% yield, erythro-form >95%) as a colorless solid.

Workup

  1. customquenched with water (1 L)
  2. extractionThe resulting mixture was extracted with EtOAc (300 ml×3)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. washThe residue was washed with petroleum ether/EtOAc (100 mL, 10:1)

Sources & evidence

ORD record
ord-ddb16bcfec904336af79c0b7591c2cee
Source dataset
uspto-grants-2016_09
Patent number
US09434761B2

Reaction notes

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