Ammonium Chloride → HCID 67105487, compound

HRID 1173595Notes

Reaction equation

HRID 1173595 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH3:23])[C:13](=[O:22])[C:14]([CH3:21])([CH3:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].[Cl-].[NH4+]>CO>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH3:23])[CH:13]([OH:22])[C:14]([CH3:21])([CH3:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 59556868HCID 59556868, compound

Product 1

HCID 67105487HCID 67105487, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of ethyl(4S)-4-{[(benzyloxy)carbonyl]amino}-2,2-dimethyl-3-oxopentanoate (905 mg) in methanol (30 mL) was cooled to 0° C., 90% sodium borohydride (180 mg) was added, and the mixture was stirred at 0° C. for 2 hr. Saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=30/1→1/3) to give ethyl(4S)-4-{[(benzyloxy)carbonyl]amino}-2,2-dimethyl-3-hydroxypentanoate as a colorless oil (yield: 720 mg, 79%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=30/1→1/3)

Sources & evidence

ORD record
ord-160531f9353f48cd91e83cf33e134add
Source dataset
uspto-grants-2010_11
Patent number
US07834051B2

Reaction notes

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