Potassium Carbonate → HCID 131715822, compound

HRID 2292049Notes

Reaction equation

HRID 2292049 reaction equation
C(OC[C:6]1[CH2:13][S:12][C@H:11]2[N:8]([C:9](=[O:18])[C@H:10]2[NH:14][C:15]([NH2:17])=[S:16])[C:7]=1[C:19]([O:21][CH:22]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20])(=O)C.Br[CH2:36][C:37](=O)[C:38]([O:40][CH2:41][CH3:42])=[O:39].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:41]([O:40][C:38]([C:37]1[N:17]=[C:15]([NH:14][CH:10]2[C:9](=[O:18])[N:8]3[CH:11]2[S:12][CH2:13][CH:6]=[C:7]3[C:19]([O:21][CH:22]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[O:20])[S:16][CH:36]=1)=[O:39])[CH3:42]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 66144Ethyl bromopyruvateHCID 14349717HCID 14349717, compound

Product 1

HCID 131715822HCID 131715822, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 450 mg of (6R-trans)-3-[(acetyloxy)methyl]-7-[(aminothioxomethyl)amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, diphenylmethyl ester, 195 mg of 3-bromo-2-oxopropanoic acid, ethyl ester, 70 mg of potassium carbonate and 7 ml of acetonitrile was stirred overnight and then filtered through hydrous magnesium silicate. The filtrate was evaporated, giving 510 mg of (6R-trans)-3-[acetyloxy)methyl]-7-[[4-(ethoxycarbonyl)-2-thiazolyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, diphenylmethyl ester.

Workup

  1. filtrationfiltered through hydrous magnesium silicate
  2. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-803b656b733145eface9ac073e472d2b
Source dataset
uspto-grants-1989_01
Patent number
US04800199

Reaction notes

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