HCID 58222080, compound → HCID 58222054, compound

HRID 1192365Notes

Reaction equation

HRID 1192365 reaction equation
C([O:3][C:4](=[O:29])[CH:5]([N:15]=C(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=1[CH3:14])C>Cl>[NH2:15][CH:5]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=1[CH3:14])[C:4]([OH:29])=[O:3]

Participants

3

Reactant 1

HCID 58222080HCID 58222080, compound

Product 1

HCID 58222054HCID 58222054, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture containing 2-(Benzhydrylidene-amino)-3-(4-chloro-2-methyl-phenyl)-propionic acid ethyl ester (1.7 g, 4.2 mmol) and 90 mL of 3N HCl was heated at 75 C overnight. The reaction was cooled to room temperature and washed with ethyl acetate. The aqueous phase was concentrated under reduced pressure to afford 2-Amino-3-(4-chloro-2-methyl-phenyl)-propionic acid (640 mg, 72%) as white solid. LCMS (APCI+) m/z 214 [M+H]+; Rt: 1.83 min. 1H NMR (D2O, 400 MHz) δ 7.18 (1H, s), 7.11 (1H, d, J 8.7 Hz), 7.05 (1H, d, J 8.3 Hz), 4.05-4.00 (1H, m), 3.23 (1H, dd, J 14.3 and 6.1 Hz), 2.98 (1H, dd, J 14.4 and 8.5 Hz), 2.19 (3H, s.)

Workup

  1. temperaturewas heated at 75 C overnight
  2. washwashed with ethyl acetate
  3. concentrationThe aqueous phase was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8eb68304a1b54d90afb30154cb235b32
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

Loading…