7-Amino-3-methyl-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid → (Pivaloyloxy)methyl (6R-trans)-7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate

HRID 839145

Reaction equation

HRID 839145 reaction equation
CN(C)[CH:3]=[O:4].[Na].[NH2:7][CH:8]1[C:15](=[O:16])[N:14]2[CH:9]1[S:10][CH2:11][C:12]([CH3:20])=[C:13]2[C:17]([OH:19])=[O:18].ClC[CH2:23][C:24]([CH3:29])([CH3:28])[C:25]([O-])=[O:26]>C(OC(=O)C)C>[C:25]([O:4][CH2:3][O:18][C:17]([C:13]1[N:14]2[CH:9]([S:10][CH2:11][C:12]=1[CH3:20])[CH:8]([NH2:7])[C:15]2=[O:16])=[O:19])(=[O:26])[C:24]([CH3:29])([CH3:28])[CH3:23]

Participants

6

Reactant 4

HCID 18837-Amino-3-methyl-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acidHCID 6228DimethylformamideHCID 5360545SodiumHCID 217530474-Chloro-2,2-dimethylbutanoate

Product 1

HCID 119617(Pivaloyloxy)methyl (6R-trans)-7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

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

Sources & evidence

ORD record
ord-a09ab6c8851f4498976bb7b89eb2d03f
Source dataset
uspto-grants-1978_06
Patent number
US04093804

Linked notes

Loading…