2-Benzhydryloxycarbonyl-7-t-butoxycarbonylamino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene → 2-Benzhydryloxycarbonyl-7-t-butoxycarbonylamino-3-(2-dimethylaminoprop-1-en-1-yl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene

HRID 463577Notes

Reaction equation

HRID 463577 reaction equation
[CH3:1][N:2]([CH3:7])[C:3](OC)=[CH2:4].[CH:8]([O:21][C:22]([C:24]1[N:25]2[CH:28]([S:29][CH2:30][C:31]=1[CH3:32])[CH:27]([NH:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[C:26]2=[O:41])=[O:23])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>CN(C)C=O>[CH:8]([O:21][C:22]([C:24]1[N:25]2[CH:28]([S:29][CH2:30][C:31]=1[CH:32]=[C:3]([N:2]([CH3:7])[CH3:1])[CH3:4])[CH:27]([NH:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[C:26]2=[O:41])=[O:23])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 128967622-Benzhydryloxycarbonyl-7-t-butoxycarbonylamino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-eneHCID 132844661-Methoxy-N,N-dimethylethen-1-amine

Product 1

HCID 545303942-Benzhydryloxycarbonyl-7-t-butoxycarbonylamino-3-(2-dimethylaminoprop-1-en-1-yl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Dimethylamino-1-methoxyethylene (218 g) is added dropwise, in the course of 55 minutes, to a solution of 2-benzhydryloxycarbonyl-7-t-butoxycarbonylamino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene (345 g) in anhydrous dimethylformamide (1,600 cc) at 80° C. This yields a solution of 2-benzhydryloxycarbonyl-7-t-butoxycarbonylamino-3-(2-dimethylaminoprop-1-en-1-yl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene, which is poured into a stirred mixture of distilled water (2 liters), ice (2 kg) and ethyl acetate (2.5 liters). The organic phase is decanted, washed with distilled water (3×1 liter), dried over sodium sulphate and concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 30° C. The residue is divided into 2 equal parts which are each chromatographed separately on a column of Merck silica gel (0.06-0.2) (1,500 g) (diameter of the column: 8.5 cm; height: 70 cm). Each column is eluted with a 23/77 (by volume) ethyl acetate/cyclohexane mixture (20 liters), 1 liter fractions being collected. Fractions 7 to 15 from each column are concentrated to dryness at 30° C. under reduced pressure (20 mm Hg; 2.7 kPa). This yields 3-acetonyl-2-benzhydryloxycarbonyl-7-t-butoxycarbonylamino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene (149 g) in the form of a hard yellow foam.

Sources & evidence

ORD record
ord-1a3ac55de4f849bd851aba231d7cb5d3
Source dataset
uspto-grants-1985_05
Patent number
US04520193

Reaction notes

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