Toluene → Methyl 3-amino-3-methylbutanoate

HRID 600915Notes

Reaction equation

HRID 600915 reaction equation
[NH2:1][C:2]([CH3:8])([CH3:7])[CH2:3][C:4]([OH:6])=[O:5].S(Cl)(Cl)=O.[C:13]1(C)C=CC=CC=1>CO>[NH2:1][C:2]([CH3:8])([CH3:7])[CH2:3][C:4]([O:6][CH3:13])=[O:5]

Participants

5

Reactant 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 27609333-Amino-3-methylbutanoic acid

Product 1

HCID 18667677Methyl 3-amino-3-methylbutanoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 3-amino-3-methyl-butyric acid 10-1 (1 eq.) in methanol at 0° C. was added 2 eq. of thionyl chloride. The reaction mixture was warmed to room temperature and stirred overnight. The solvent was evaporated to give azeotropic mixture of 10-2 and toluene (x=3) which was used for Step B. MS: MH+=132.1

Workup

  1. customThe solvent was evaporated
  2. customto give azeotropic

Sources & evidence

ORD record
ord-bb6106fff1594252865d9d33fdecda9a
Source dataset
uspto-grants-2011_03
Patent number
US07902240B2

Reaction notes

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