1-Methoxy-N,N-dimethylethen-1-amine → 7-t-Butoxycarbonylamino-3-(2-dimethylaminoprop-1-en-1-yl)-2-(4-methoxybenzyloxycarbonyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene

HRID 463576Notes

Reaction equation

HRID 463576 reaction equation
[CH3:1][N:2]([CH3:7])[C:3](OC)=[CH2:4].[C:8]([O:12][C:13]([NH:15][CH:16]1[C:23](=[O:24])[N:22]2[CH:17]1[S:18][CH2:19][C:20]([CH3:37])=[C:21]2[C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=1)=[O:26])=[O:14])([CH3:11])([CH3:10])[CH3:9]>CN(C)C=O>[C:8]([O:12][C:13]([NH:15][CH:16]1[C:23](=[O:24])[N:22]2[CH:17]1[S:18][CH2:19][C:20]([CH:37]=[C:3]([N:2]([CH3:7])[CH3:1])[CH3:4])=[C:21]2[C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=1)=[O:26])=[O:14])([CH3:11])([CH3:10])[CH3:9]

Participants

4

Reactant 2

HCID 132844661-Methoxy-N,N-dimethylethen-1-amineHCID 202811257-t-Butoxycarbonylamino-2-(4-methoxybenzyloxycarbonyl)-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene

Product 1

HCID 541001667-t-Butoxycarbonylamino-3-(2-dimethylaminoprop-1-en-1-yl)-2-(4-methoxybenzyloxycarbonyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

1-Dimethylamino-1-methoxyethylene (4 cc) is added, in the course of 55 minutes, to a solution of 7-t-butoxycarbonylamino-2-(4-methoxybenzyloxycarbonyl)-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene (3.75 g) in dimethylformamide (25 cc), heated to 80° C., the temperature being kept at 80° C. This yields a solution of 7-t-butoxycarbonylamino-3-(2-dimethylaminoprop-1-en-1-yl)-2-(4-methoxybenzyloxycarbonyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene, which is poured into a mixture of iced water (20 cc) and ethyl acetate (150 cc). The organic phase is washed with water (2×200 cc), dried over sodium sulphate and filtered in the presence of decolorising charcoal and the filtrate is evaporated to dryness under reduced pressure (20 mm Hg; 2.7 kPa). The residue is chromatographed on a column of Merck silica gel (0.06-0.2) (45 g) (diameter of the column: 3 cm, height: 15 cm). Elution is carried out with a 20/80 (by volume) ethyl acetate/cyclohexane mixture (500 cc) and 40 cc fractions are collected. Fractions 7 to 10 are concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) and this yields a mixture (70/30) of 3-acetonyl-7-t-butoxycarbonylamino-2-(4-methoxybenzyloxycarbonyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene and -oct-3-ene (0.25 g) in the form of an ochre solid.

Workup

  1. custombeing kept at 80° C

Sources & evidence

ORD record
ord-81d6f409882d4a3d8a7fa7bfbaa6e0d0
Source dataset
uspto-grants-1985_05
Patent number
US04520193

Reaction notes

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