Acetic Acid → HCID 131712810, compound

HRID 1702709Notes

Reaction equation

HRID 1702709 reaction equation
[CH3:1][C:2]1[C:3](=[O:21])[C@@H:4]2[CH2:19][C:18](=[O:20])[N:5]2[C:6]=1[C:7]([O:9][CH2:10][O:11][C:12](=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14])=[O:8].[BH4-].C([N+](CCCC)(CCCC)CCCC)CCC.C(O)(=O)C>C(Cl)Cl>[OH:21][CH:3]1[C@@H:4]2[CH2:19][C:18](=[O:20])[N:5]2[C:6]([C:7]([O:9][CH2:10][O:11][C:12](=[O:17])[C:13]([CH3:15])([CH3:14])[CH3:16])=[O:8])=[C:2]1[CH3:1]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 169536Tetrabutylammonium borohydrideHCID 13065655HCID 13065655, compound

Product 1

HCID 131712810HCID 131712810, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

Pivaloyloxymethyl 2-diazo-3-methyl-1-betaoxoceph-3-em-4-carboxylate (150 mg., 0.42 mmoles) was converted to a methylene chloride solution of pivaloyloxymethyl 2-methyl-1-oxocarbapen-2-em-3-carboxylate by the method of Example 1. Without isolation, and while continuing to maintain the temperature at -78° C., tetrabutylammonium borohydride (26.4 mg., 0.092 mmole) was added and the mixture stirred for 30 minutes. The reaction was quenched with acetic acid (0.58 equivalent), extracted twice with aqueous buffer (pH 7), dried over anhydrous sodium sulfate and filtered to yield a methylene chloride solution of pivaloyloxymethyl 1-hydroxy-2-methylcarbapen-2-em-3-carboxylate [ir (CH2Cl2) 1780, 1745 cm-1 ; Rf 0.25, (4:1 chloroform:ethyl acetate)]. If desired, this product is further isolated by evaporation in vacuo, keeping the temperature as low as possible to minimize degradation.

Workup

  1. extractionextracted twice with aqueous buffer (pH 7)
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered

Sources & evidence

ORD record
ord-c76264ab8bbd444eb387af8b8f5cffc7
Source dataset
uspto-grants-1982_09
Patent number
US04348264

Reaction notes

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