Tetrabutylammonium borohydride → HCID 70507546, compound

HRID 1702723Notes

Reaction equation

HRID 1702723 reaction equation
[CH3:1][O:2][C:3]1([NH:24][C:25](=[O:34])[CH2:26][O:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22](=[O:23])[N:5]2[CH:6]([C:11]([O:13][CH2:14][O:15][C:16](=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18])=[O:12])[CH:7]([CH3:10])[C:8](=[O:9])[C@H:4]12.[BH4-].C([N+](CCCC)(CCCC)CCCC)CCC>C(Cl)Cl>[OH:9][CH:8]1[C@@H:4]2[C:3]([O:2][CH3:1])([NH:24][C:25](=[O:34])[CH2:26][O:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:22](=[O:23])[N:5]2[CH:6]([C:11]([O:13][CH2:14][O:15][C:16](=[O:21])[C:17]([CH3:19])([CH3:18])[CH3:20])=[O:12])[CH:7]1[CH3:10]

Participants

4

Reactant 2

HCID 169536Tetrabutylammonium borohydrideHCID 70507526HCID 70507526, compound

Product 1

HCID 70507546HCID 70507546, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pivaloyloxymethyl 6-methoxy-2-methyl-1-oxo-6-(2-phenoxyacetamido)carbapenam-3-carboxylate (79 mg., 0.17 mmole) in 10 ml. of methylene chloride was reduced at -78° C. with tetrabutylammonium borohydride (11 mg., 0.04 mmole), the reaction monitored, and crude product isolated according to Example 3. Chromatography on silica gel (3:1 methylene chloride:ethyl acetate as eluant), monitored by ir, gave pivaloyloxymethyl 1-hydroxy-6-methoxy-2-methyl-6-(2-phenoxyacetamido)carbapenam-3-carboxylate [9.8 mg., 12%; Rf 0.3 (4:1 chloroform:ethyl acetate); ir (CH2Cl2) 1770, 1750, 1670 cm-1 ].

Workup

  1. customcrude product isolated

Sources & evidence

ORD record
ord-3d0406a796fc41578eb51e0543d139b0
Source dataset
uspto-grants-1982_09
Patent number
US04348264

Reaction notes

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