Water → 5-Tert-butoxycarbonylamino-2-hydroxy-pentanoic acid methyl ester

HRID 899044Notes

Reaction equation

HRID 899044 reaction equation
CI.[C:3]([O:7][C:8]([NH:10][CH2:11][CH2:12][CH2:13][CH:14]([OH:18])[C:15]([OH:17])=[O:16])=[O:9])([CH3:6])([CH3:5])[CH3:4].[C:19]([O-])(O)=O.[Na+].O>CN(C=O)C>[CH3:19][O:16][C:15](=[O:17])[CH:14]([OH:18])[CH2:13][CH2:12][CH2:11][NH:10][C:8]([O:7][C:3]([CH3:6])([CH3:4])[CH3:5])=[O:9]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 516892Sodium BicarbonateHCID 190762575-{[(Tert-butoxy)carbonyl]amino}-2-hydroxypentanoic acid

Product 1

HCID 543300255-Tert-butoxycarbonylamino-2-hydroxy-pentanoic acid methyl esterYield 42.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of methyl iodide (11.5 mL, 0.189 mol) in DMF (50 mL) was added dropwise during 15 min. to a mixture of 5-tert-butoxycarbonylamino-2-hydroxy-pentanoic acid (22.0 g, 94.4 mmol) and NaHCO3 (11.8 g, 141 mmol) in DMF (150 mL). After stirring over night, water was added and the mixture was extracted with ethyl acetate. The pooled organic phases were washed with water and brine, dried and concentrated under reduced pressure. The crude product was purified using chromatography (heptane/ethyl acetate, 1:1) to give 5-tert-butoxycarbonylamino-2-hydroxy-pentanoic acid methyl ester 9.9 g, 42.5%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe pooled organic phases were washed with water and brine
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified

Sources & evidence

ORD record
ord-e87be85b452549a48dc345c93e014d37
Source dataset
uspto-grants-2008_04
Patent number
US07354895B1

Reaction notes

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