Methanol → (S)-Methyl 2-(((benzyloxy)carbonyl)amino)butanoate

HRID 929934Notes

Reaction equation

HRID 929934 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:16][CH3:17])[C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:18]O>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:16][CH3:17])[C:13]([O:15][CH3:18])=[O:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 7349998(2S)-2-(((Phenylmethoxy)carbonyl)amino)butanoic acid

Product 1

HCID 10444846(S)-Methyl 2-(((benzyloxy)carbonyl)amino)butanoateYield 48%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of (S)-2-(((benzyloxy)carbonyl)amino)butanoic acid (10.0 g, 42.1 mmol) in methanol (100 mL) and toluene (300 mL) was added dropwise at room temperature under argon trimethylsilyldiazomethane (23.2 mL, 46.4 mmol). After stirring at room temperature for 1 hour, the reaction mixture was concentrated and the residue was extracted with a solution of EtOAc and brine. The combined organic layers were dried over Na2SO4, filtered and the filtrate was concentrated. The residue was purified by column chromatography (120 g SiO2) using EtOAc in hexane from 0% to 30% in order to give the title compound (5.2 g, 48%) as a colorless oil. LC-MS: [M+H] 252.1; Rt 0.93 min; (LCMS method 1).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. extractionthe residue was extracted with a solution of EtOAc and brine
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by column chromatography (120 g SiO2)

Sources & evidence

ORD record
ord-e7fbe75c337a42d5b27d29a09f6dcf0f
Source dataset
uspto-grants-2016_03
Patent number
US09296733B2

Reaction notes

Loading…