methyl N-acetyl-3-(2-naphthyl)-D-alaninate → D-3-(2-Naphthyl)alanine

HRID 904613Notes

Reaction equation

HRID 904613 reaction equation
C([NH:4][C@@H:5]([C:17]([O:19]C)=[O:18])[CH2:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=1)(=O)C>Cl>[CH:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:15]=[CH:16][C:7]=1[CH2:6][C@H:5]([C:17]([OH:19])=[O:18])[NH2:4]

Participants

3

Reactant 1

HCID 9878585methyl N-acetyl-3-(2-naphthyl)-D-alaninate

Product 1

HCID 2733661D-3-(2-Naphthyl)alanineYield 60.5%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 2.5 g of methyl N-acetyl-3-(2-naphthyl)-D-alaninate in 60 ml of 6N HCl was heated at 120°-130° for 3 hours and cooled to room temperature. The white precipitate which formed was collected and recrystallized from 50 ml of H2O containing 1 ml of 12N HCl by neutralization with NH4OH to pH 6, and dried in vacuo to yield 1.2 g of 3-(2-naphthyl)-D-alanine, m.p. 242°-244°, [α]D25 26.6° (c 0.5, CH3CO2H).

Workup

  1. customThe white precipitate which formed
  2. customwas collected
  3. customrecrystallized from 50 ml of H2O containing 1 ml of 12N HCl by neutralization with NH4OH to pH 6
  4. customdried in vacuo

Sources & evidence

ORD record
ord-3ff7ea52106841869dc7f3c050e7ea5b
Source dataset
uspto-grants-1983_12
Patent number
US04419347

Reaction notes

Loading…