L-Lysine → 5-(4-Benzyloxycarbonylaminobutyl)-3-methyl-2-thiohydantoin

HRID 1287290

반응식

HRID 1287290 반응식
CO[C:3](=[O:21])[C@H:4]([CH2:6][CH2:7][CH2:8][CH2:9][NH:10][C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[NH2:5].N[C@H](C(O)=O)CCCCN.[CH3:32][N:33]=[C:34]=[S:35]>C(#N)C>[CH2:14]([O:13][C:11]([NH:10][CH2:9][CH2:8][CH2:7][CH2:6][CH:4]1[NH:5][C:34](=[S:35])[N:33]([CH3:32])[C:3]1=[O:21])=[O:12])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

참가 물질

5

반응물 3

HCID 5962L-LysineHCID 11167Methyl isothiocyanateHCID 6994982methyl (2S)-2-amino-6-(phenylmethoxycarbonylamino)hexanoate

생성물 1

HCID 215076825-(4-Benzyloxycarbonylaminobutyl)-3-methyl-2-thiohydantoin수율 22.4%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A solution of Nε-benzyloxycarbonyl-L-lysine methyl ester (4.66 g., 0.016 mol.) (prepared from L-lysine according to the method of Bergmann et al., J. Biol. Chem. 1935, 111, 245) in acetonitrile (20 ml.) was treated with methyl isothiocyanate (1.16 g., 0.016 mol.) and the mixture heated at reflux for 3 hours. The solvent was removed in vacuo and the residual oil triturated with ethanol to give a white solid which recrystallised from ethanol to give the title compound as colourless needles (1.2 g.) m.p. 135°C. (Found: C, 57.3; H, 6.4; N, 12.2; C16H21N3O3S requires: C, 57.3; H, 6.3; N, 12.5%).

후처리

  1. temperaturethe mixture heated
  2. temperatureat reflux for 3 hours
  3. customThe solvent was removed in vacuo
  4. customthe residual oil triturated with ethanol
  5. customto give a white solid which
  6. customrecrystallised from ethanol

출처 및 근거

ORD 기록
ord-ac5d9645333b464685fd8da40dd721f4
출처 데이터셋
uspto-grants-1976_10
특허 번호
US03984430

연결된 노트

불러오는 중…