Acetic Acid → HCID 131712812, compound

HRID 1702714Notes

Reaction equation

HRID 1702714 reaction equation
[CH3:1][C:2]1[C:3](=[O:18])[C@@H:4]2[CH2:16][C:15](=[O:17])[N:5]2[C:6]=1[C:7]([O:9][CH2:10][C:11]([Cl:14])([Cl:13])[Cl:12])=[O:8].[BH4-].C[N+](C)(C)C.C(O)(=O)C>C(Cl)Cl>[OH:18][CH:3]1[C@@H:4]2[CH2:16][C:15](=[O:17])[N:5]2[C:6]([C:7]([O:9][CH2:10][C:11]([Cl:14])([Cl:12])[Cl:13])=[O:8])=[C:2]1[CH3:1]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 28122N,N,N-Trimethylmethanaminium tetrahydroborateHCID 131712813HCID 131712813, compound

Product 1

HCID 131712812HCID 131712812, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Freshly prepared 2,2,2-trichloroethyl 2-methyloxocarbapen-2-em-3-carboxylate, made from 100 mg. (0.317 mmole) of the precursor oxide according to Example 11, was taken up in 2 ml. of methylene chloride and cooled to -78° C. Tetramethylammonium borohydride (23 mg., 0.079 mmole) was added. After 30 minutes, ir spectral analysis (1775 cm-1) indicated a satisfactory reduction. The reaction was quenched with acetic acid (0.58 equivalent, 10 microl.), extracted twice with aqueous buffer solution (pH 7), dried over anhydrous magnesium sulfate and filtered to yield a solution of 2,2,2-trichloroethyl 1-hydroxy-2-methylcarbapen-2-em-3-carboxylate. If desired, this product is further isolated by evaporation to dryness in vacuo at reduced temperature.

Workup

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

Sources & evidence

ORD record
ord-a93ffd03fa784397b8c0167117776f0f
Source dataset
uspto-grants-1982_09
Patent number
US04348264

Reaction notes

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