반응 #566803

ord-db8b44ffaca7458a970d011ed2501600

반응 방정식

Cl.N[C@@H](CS)C(=O)O
L-(+)-cysteine hydrochloride
CC(=O)[O-].O.O.O.[Na+]
natriumacetate trihydrate
N#Cc1ccc(C=O)cc1
4-Cyanobenzaldehyde
N#Cc1ccc(C2N[C@H](C(=O)O)CS2)cc1
2-(RS)-(4-cyanophenyl)thiazolidine-4-(R)-carboxylic acid
수율 44.9%

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    workup.ADDITIONwas added
  2. 2
    여과the white crystals were collected by filtration
  3. 3
    세척washed twice with 15 ml of water:ethanol (1:1)

실험 절차

4-Cyanobenzaldehyde (500 mg, 3.8 mmol) was dissolved in 5 ml of ethanol (96%) and L-(+)-cysteine hydrochloride (460 mg, 3.8 mmol) and natriumacetate trihydrate (468 mg, 5.7 mmol) dissolved in 5 ml of water was added. The reaction mixture was stirred for 16 hours at room temperature and the white crystals were collected by filtration and washed twice with 15 ml of water:ethanol (1:1), to afford 400 mg of 2-(RS)-(4-cyanophenyl)thiazolidine-4-(R)-carboxylic acid (48) in 44% yield. 1H-NMR (MEOH, 300 MHz) δ: 7.69 (m, 4H); 5.81 (s, ½H); 5.60 (s, ½H); 4.23 (dd, ½H); 4.02 (dd, ½H); 3.52-3.17 (m, 2H).

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US06645995B2uspto-grants-2003_11