Dimethylformamide → 3-[(Acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid propionyloxymethyl ester

HRID 1604912Notes

Reaction equation

HRID 1604912 reaction equation
CN(C)C=O.[Na].[C:7]([O:10][CH2:11][C:12]1[CH2:19][S:18][CH:17]2[N:14]([C:15](=[O:21])[CH:16]2[NH2:20])[C:13]=1[C:22]([OH:24])=[O:23])(=[O:9])[CH3:8].Cl[CH2:26][O:27][C:28](=[O:31])[CH2:29][CH3:30]>C(OCC)(=O)C>[C:28]([O:27][CH2:26][O:23][C:22]([C:13]1[N:14]2[CH:17]([S:18][CH2:19][C:12]=1[CH2:11][O:10][C:7](=[O:9])[CH3:8])[CH:16]([NH2:20])[C:15]2=[O:21])=[O:24])(=[O:31])[CH2:29][CH3:30]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 137293-((Acetyloxy)methyl)-7-amino-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acidHCID 221144Chloromethyl propionateHCID 5360545Sodium

Product 1

HCID 214259953-[(Acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid propionyloxymethyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 35 ml of dimethyl formamide is added 7.5 g of the sodium salt of 3-[(acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, and the solution is stirred at room temperature for about 30 minutes after which 8 ml of chloromethylpropionate is added. Stirring is continued at room temperature for about 3 hours. The mixture is diluted with ethyl acetate and washed with water. The organic layer is separated and evaporated to dryness. The residue is recrystallized from ethyl acetate to give 3-[(acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0 ]oct-2-ene-2-carboxylic acid propionyloxymethyl ester

Workup

  1. additionis added
  2. washwashed with water
  3. customThe organic layer is separated
  4. customevaporated to dryness
  5. customThe residue is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-d2ec1eda3b234d28b7242ccdcd443fd2
Source dataset
uspto-grants-1976_04
Patent number
US03948904

Reaction notes

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