Ethyl Acetate → HCID 20281155, compound

HRID 463592Notes

Reaction equation

[CH:1]([O:14][C:15]([C:17]1[N:18]2[CH:21]([S:22](=[O:34])[CH2:23][C:24]=1[CH2:25][C:26]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:27])[CH:20]([NH:35]C(OC(C)(C)C)=O)[C:19]2=[O:43])=[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.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>C(#N)C>[NH2:35][CH:20]1[C:19](=[O:43])[N:18]2[CH:21]1[S:22](=[O:34])[CH2:23][C:24]([CH2:25][C:26]([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)=[O:27])=[C:17]2[C:15]([O:14][CH:1]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:16]

Participants

Conditions

Temperature: 35 °C

Procedure

2-Benzhydryloxycarbonyl-7-t-butoxycarbonylamino-8-oxo-3-phenacyl-5-thia-1-azabicyclo[4.2.0]oct-2-ene-5-oxide (10.1 g) is added to a solution of p-toluenesulphonic acid monohydrate (8.15 g) in acetonitrile (170 cc), warmed to 35° C., and the mixture is left at 35° C. for 1 hour, whilst stirring. The reaction mixture is then poured into a stirred mixture of a saturated solution of sodium bicarbonate (150 cc) and ethyl acetate (300 cc). The organic phase is then washed with distilled water (100 cc), dried over magnesium sulphate and evaporated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 20° C. This yields crude 7-amino-2-benzhydryloxycarbonyl-8-oxo-3-phenacyl-5-thia-1-azabicyclo[4.2.0]oct-2-ene-5-oxide (7 g) in the form of a thick oil which can be used without purification.

Workup

washThe organic phase is then washed with distilled water (100 cc)
dry with materialdried over magnesium sulphate
customevaporated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 20° C

Sources & evidence

ORD record: ord-5745a487c5fb4423b76afc338a56a022
Source dataset: uspto-grants-1985_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04520193

Reaction notes

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