Acetic Acid → HCID 69853737, compound

HRID 987930Notes

Reaction equation

HRID 987930 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:12]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:11]([CH2:20][C:21](=[O:28])[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[O:10][C:9]1([CH3:30])[CH3:29])=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].C(O)(=O)C>C(O)C>[C:1]([O:5][C:6]([N:8]1[CH:12]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:11]([CH2:20][CH:21]([OH:28])[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[O:10][C:9]1([CH3:29])[CH3:30])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 69853645HCID 69853645, compound

Product 1

HCID 69853737HCID 69853737, compoundYield 100.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-benzyl-5-(3-ethoxycarbonyl-2-oxo-propyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (10 g) in ethanol (100 ml) was stirred at 15° C. under an atmosphere of nitrogen during the portion-wise addition of sodium borohydride (450 mg). The solution was stirred for a further 30 minutes, treated with glacial acetic acid (2 ml) and evaporated. The residue was partitioned between diethyl ether (200 ml) and 2M aqueous hydrochloric acid (100 ml). The organic solution was washed sequentially with water, 5% aqueous sodium bicarbonate solution, water and saturated aqueous sodium chloride solution, dried (anhydrous magnesium sulfate) and evaporated to give 4-benzyl-5-(3-ethoxycarbonyl-2-hydroxy-propyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (10.11 g, 100%). Mass spectrum 422 [M+H]+.

Workup

  1. customevaporated
  2. customThe residue was partitioned between diethyl ether (200 ml) and 2M aqueous hydrochloric acid (100 ml)
  3. washThe organic solution was washed sequentially with water, 5% aqueous sodium bicarbonate solution, water and saturated aqueous sodium chloride solution
  4. dry with materialdried (anhydrous magnesium sulfate)
  5. customevaporated

Sources & evidence

ORD record
ord-e138539883cd4fc29c901d568416f0b8
Source dataset
uspto-grants-2003_10
Patent number
US06632826B1

Reaction notes

Loading…