Cysteine Hydrochloride → 2-(RS)-(4-cyanophenyl)thiazolidine-4-(R)-carboxylic acid

HRID 479621

반응식

HRID 479621 반응식
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1)#[N:2].Cl.[NH2:12][C@H:13]([C:16]([OH:18])=[O:17])[CH2:14][SH:15].O.O.O.C([O-])(=O)C.[Na+]>C(O)C.O>[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]2[NH:12][C@H:13]([C:16]([OH:18])=[O:17])[CH2:14][S:15]2)=[CH:5][CH:4]=1)#[N:2]

참가 물질

6

반응물 3

HCID 60960Cysteine HydrochlorideHCID 660424-CyanobenzaldehydeHCID 23665404Sodium Acetate Trihydrate

생성물 1

HCID 112533042-(RS)-(4-cyanophenyl)thiazolidine-4-(R)-carboxylic acid수율 44.9%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

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).

후처리

  1. additionwas added
  2. filtrationthe white crystals were collected by filtration
  3. washwashed twice with 15 ml of water:ethanol (1:1)

출처 및 근거

ORD 기록
ord-db8b44ffaca7458a970d011ed2501600
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06645995B2

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