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 2413409Notes

Reaction equation

HRID 2413409 reaction equation
[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

Participants

4

Reactant 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

Product 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

Procedure

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.

Workup

  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.

Sources & evidence

ORD record
ord-7e9597f544a04352b6ff128c5d6b2b3b
Source dataset
uspto-grants-1985_01
Patent number
US04496560

Reaction notes

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