6-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid → 6-[[Sulfo(2,3-dihydro-5-benzofuranyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Reaction equation
[S:1]([CH:5]([C:9]1[CH:10]=[CH:11][C:12]2[O:16][CH2:15][CH2:14][C:13]=2[CH:17]=1)[C:6](Cl)=[O:7])([OH:4])(=[O:3])=[O:2].[NH2:18][CH:19]1[C:25](=[O:26])[N:24]2[CH:20]1[S:21][C:22]([CH3:31])([CH3:30])[CH:23]2[C:27]([OH:29])=[O:28].O>CCOCC.C(=O)(O)[O-].[Na+]>[S:1]([CH:5]([C:9]1[CH:10]=[CH:11][C:12]2[O:16][CH2:15][CH2:14][C:13]=2[CH:17]=1)[C:6]([NH:18][CH:19]1[C:25](=[O:26])[N:24]2[CH:20]1[S:21][C:22]([CH3:31])([CH3:30])[CH:23]2[C:27]([OH:29])=[O:28])=[O:7])([OH:4])(=[O:3])=[O:2]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
Sulfo(2,3-dihydro-5-benzofuranyl)acetyl chloride (5 mmole) in 10 ml of ether is added to 5 mmole of 6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid dissolved in 10 ml of water containing 10 mmole of sodium bicarbonate. The temperature is maintained at about 0° C. during the addition. The reaction mixture is stirred for about 30 minutes at 0° C. The organic phase is separated from the aqueous phase. The pH of the aqueous phase is adjusted to 6.5 to 7.0. The aqueous phase is extracted with ethyl acetate. The ethyl acetate is dried over magnesium sulfate, filtered and evaporated to give the title compound.
Workup
- customThe organic phase is separated from the aqueous phase
- extractionThe aqueous phase is extracted with ethyl acetate
- dry with materialThe ethyl acetate is dried over magnesium sulfate
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-084f55711a964c94b88e411bf2641804
- Source dataset
- uspto-grants-1979_02
- Patent number
- US04138397
Reaction notes
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