Aminoisobutyric acid → N-Formyl-2-methylalanine

HRID 442504Notes

Reaction equation

HRID 442504 reaction equation
[NH2:1][C:2]([CH3:7])([CH3:6])[C:3]([OH:5])=[O:4].[C:8](OC(=O)C)(=[O:10])C>C(O)=O>[CH:8]([NH:1][C:2]([CH3:7])([CH3:6])[C:3]([OH:5])=[O:4])=[O:10]

Participants

4

Reactant 2

HCID 6119Aminoisobutyric acidHCID 7918Acetic Anhydride

Product 1

HCID 15683540N-Formyl-2-methylalanine

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

Preparation of ethyl-60 -aminoisobutyrylglycinate hydrochloride: To a solution of 10.3 gms (0.10 mol) of α-aminoisobutyric acid in 210 ml of 98% formic acid at 0° C, there was added dropwise with stirring 70 ml of acetic anhydride. After stirring at room temperature for 2 hr., 85 ml of ice water was added and the solution evaporated under reduced pressure to give an off-white solid. Recrystallization from absolute ethanol gave 11.2 g (0.085 mol), 85%, N-formyl-α -aminoisobutyric acid, mp 129.5°-131° C; pmr (D2O) δ 1.50 (s, 6H), 4.06 (s, 2H) and 8.16 (s, 1H) ppm.

Workup

  1. customthe solution evaporated under reduced pressure
  2. customto give an off-white solid
  3. customRecrystallization from absolute ethanol

Sources & evidence

ORD record
ord-1cfa59d52f5d4b0da30db269529cd581
Source dataset
uspto-grants-1977_08
Patent number
US04045578

Reaction notes

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