Benzyl chloroformate → (S)-2-Benzyloxycarbonylamino-3-(4-hydroxy-phenyl)-2-methyl-propionic acid methyl ester

HRID 39065

Reaction equation

HRID 39065 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:16])[C@:5]([NH2:15])([CH3:14])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1.C([O-])(O)=O.[Na+].Cl[C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24]>C(OCC)(=O)C>[CH3:2][O:3][C:4](=[O:16])[C@:5]([NH:15][C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24])([CH3:14])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 24847455(S)-Methyl 2-amino-3-(4-hydroxyphenyl)-2-methylpropanoate hydrochloride

Product 1

HCID 66719336(S)-2-Benzyloxycarbonylamino-3-(4-hydroxy-phenyl)-2-methyl-propionic acid methyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of (S)-2-amino-3-(4-hydroxy-phenyl)-2-methyl-propionic acid methyl ester hydrochloride in ethyl acetate (25 mL) was added 1N NaHCO3 solution (12.5 ml.) and the mixture was stirred rapidly at ambient temperature for the addition of neat benzyl chloroformate (0.859 g, 1.01 eq., 5.05 mmol). Following addition, the reaction mixture was stirred for an additional hour; TLC and LC-MS analysis showed the reaction to be complete. The mixture was partitioned and the organic phase was separated and dried over Na2SO4 and concentrated. The crude product was used directly in the subsequent reaction without purification.

Workup

  1. additionaddition
  2. customthe reaction
  3. customThe mixture was partitioned
  4. customthe organic phase was separated
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe crude product was used directly in the subsequent reaction without purification

Sources & evidence

ORD record
ord-20dab0b640704c31945a292db1aef8fd
Source dataset
uspto-grants-2013_09
Patent number
US08524708B2

Linked notes

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