Tetrabutylammonium borohydride → HCID 70509211, compound

HRID 2296560Notes

Reaction equation

HRID 2296560 reaction equation
[CH3:1][CH:2]1[CH:6]([C:7]([O:9][CH:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[N:5]2[C:23](=[O:36])[CH:24]([NH:25][C:26](=[O:35])[CH2:27][O:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C@H:4]2[C:3]1=[O:37].[BH4-].C([N+](CCCC)(CCCC)CCCC)CCC>C(Cl)Cl>[OH:37][CH:3]1[C@@H:4]2[CH:24]([NH:25][C:26](=[O:35])[CH2:27][O:28][C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:23](=[O:36])[N:5]2[CH:6]([C:7]([O:9][CH:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:8])[CH:2]1[CH3:1]

Participants

4

Reactant 2

HCID 169536Tetrabutylammonium borohydrideHCID 70507886HCID 70507886, compound

Product 1

HCID 70509211HCID 70509211, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

According to the procedures detailed in Example 3, benzhydryl 2-methyl-1-oxo-6-(2-phenoxyacetamido)carbapenam-3-carboxylate (138 mg., 0.28 mmole) in 15 ml. of methylene chloride was reduced with tetrabutylammonium borohydride (18 mg., 0.07 mmole) at -78° C., monitored and isolated as a washed, dried methylene chloride solution of benzhydryl 1-hydroxy-2-methyl-6-(2-phenoxyacetamido)carbapenam-3-carboxylate [Rf 0.24 (4:1 chloroform:ethyl acetate)]. If desired, the product is further isolated by evaporation to dryness in vacuo.

Sources & evidence

ORD record
ord-073a15dbf3cc457386bb68c623f16951
Source dataset
uspto-grants-1984_01
Patent number
US04429128

Reaction notes

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