Aminoisobutyric acid → N-Formyl-2-methylalanine

HRID 1658926Notes

Reaction equation

HRID 1658926 reaction equation
Cl.C(N(C(=O)C(C)C)C(N)[C:6](O)=[O:7])C.[NH2:15][C:16]([CH3:21])([CH3:20])[C:17]([OH:19])=[O:18].C(OC(=O)C)(=O)C>C(O)=O>[CH:6]([NH:15][C:16]([CH3:21])([CH3:20])[C:17]([OH:19])=[O:18])=[O:7]

Participants

5

Reactant 3

HCID 6119Aminoisobutyric acidHCID 7918Acetic AnhydrideHCID 86733614HCID 86733614, compound

Product 1

HCID 15683540N-Formyl-2-methylalanine

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

Preparation of ethyl-α -aminoisobutyrylglycinate hydrochloride: To a solution of 10.3 g (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-b1fee7f71f204db183c09f66902d54f4
Source dataset
uspto-grants-1976_06
Patent number
US03966796

Reaction notes

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