Methylthiourea → 2-Benzhydryloxycarbonyl-7-t-butoxycarbonylamino-3-(2-methylamino-thiazol-5-yl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene

HRID 2413409노트

반응식

HRID 2413409 반응식
[CH:1]([O:14][C:15]([C:17]1[N:18]2[CH:21]([S:22][CH2:23][C:24]=1[C:25]1[S:29][C:28]([NH:30][CH3:31])=[N:27][CH:26]=1)[CH:20]([NH:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])O2)=[O:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CNC(N)=S.[CH:45]([O:58]C(C1N2C(SCC=1C=CN(C)C)C(NC(OC(C)(C)C)=O)C2=O)=O)(C1C=CC=CC=1)C1C=CC=CC=1>>[CH:1]([O:14][C:15]([C:17]1[N:18]2[CH:21]([S:22][CH2:23][C:24]=1[C:25]1[S:29][C:28]([NH:30][CH3:31])=[N:27][CH:26]=1)[CH:20]([NH:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[C:45]2=[O:58])=[O:16])([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

참가 물질

4

반응물 3

HCID 2723704MethylthioureaHCID 204304382-Benzhydryloxycarbonyl-7-t-butoxycarbonylamino-3-(2-methylamino-thiazol-5-yl)-8-oxa-5-thia-1-azabicyclo[4.2.0]oct-2-eneHCID 539143342-Benzhydryloxycarbonyl-7-t-butoxycarbonylamino-3-(2-dimethylamino-vinyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene

생성물 1

HCID 204304072-Benzhydryloxycarbonyl-7-t-butoxycarbonylamino-3-(2-methylamino-thiazol-5-yl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene

실험 절차

2-Benzhydryloxycarbonyl-7-t-butoxycarbonylamino-3-(2-methylamino-thiazol-5-yl)-8-oxa-5-thia-1-azabicyclo[4.2.0]oct-2-ene can be prepared by following the working method of Example 2, but replacing the thiourea by N-methylthiourea (4 g). Starting from 2-benzhydryloxycarbonyl-7-t-butoxycarbonylamino-3-(2-dimethylamino-vinyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene (E-form)(20 g), and following purification by chromatography on a column (height: 45 cm, diameter: 4 cm) of silica gel (0.2-0.06 mm), elution being carried out with mixtures of cyclohexane and ethyl acetate, successively 50:50 by volume (1.5 liters), 40:60 by volume (1 liter) and 20:80 by volume (1.5 liters), and then with ethyl acetate (1 liter), and the fractions containing the expected product (according to thin layer chromatography) being combined and evaporated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 30° C., 2-benzhydryloxycarbonyl-7-t-butoxycarbonylamino-3-(2-methylamino-thiazol-5-yl)-8-oxo-5-thia- 1-azabicyclo[4.2.0]oct-2-ene (4.74 g) is obtained in the form of a pale brown froth.

후처리

  1. custompurification by chromatography
  2. washon a column (height: 45 cm, diameter: 4 cm) of silica gel (0.2-0.06 mm), elution
  3. additionwith ethyl acetate (1 liter), and the fractions containing the expected product (according to thin layer chromatography)
  4. customevaporated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 30° C.

출처 및 근거

ORD 기록
ord-7e9597f544a04352b6ff128c5d6b2b3b
출처 데이터셋
uspto-grants-1985_01
특허 번호
US04496560

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