Tetrabutylammonium borohydride → HCID 70508934, compound

HRID 2296558Notes

Reaction equation

HRID 2296558 reaction equation
[CH3:1][CH:2]1[CH:6]([C:7]([O:9][CH2:10][O:11][C:12](=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14])=[O:8])[N:5]2[C:18](=[O:31])[CH:19]([NH:20][C:21](=[O:30])[CH2:22][O:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C@H:4]2[C:3]1=[O:32].[BH4-].C([N+](CCCC)(CCCC)CCCC)CCC>C(Cl)Cl>[OH:32][CH:3]1[C@@H:4]2[CH:19]([NH:20][C:21](=[O:30])[CH2:22][O:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:18](=[O:31])[N:5]2[CH:6]([C:7]([O:9][CH2:10][O:11][C:12](=[O:17])[C:13]([CH3:15])([CH3:14])[CH3:16])=[O:8])[CH:2]1[CH3:1]

Participants

4

Reactant 2

HCID 169536Tetrabutylammonium borohydrideHCID 70507356HCID 70507356, compound

Product 1

HCID 70508934HCID 70508934, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

By the procedures of Examples 3 and 6, pivaloyloxymethyl 2-methyl-1-oxo-6-(2-phenoxyacetamido)carbapenam-3-carboxylate (102 mg., 0.23 mmole) in 3 ml. of methylene chloride was reduced by the action of tetrabutylammonium borohydride (15 mg., 0.06 mmole) and isolated to yield purified pivaloyloxymethyl 1-hydroxy-2-methyl-6-(2-phenoxyacetamido)carbapenam-3-carboxylate [68 mg.; Rf 0.26 (4:1 chloroform:ethyl acetate; ir (CH2Cl2) 1775, 1750, 1675 cm-1 ].

Workup

  1. customisolated
  2. customto yield
  3. custompurified pivaloyloxymethyl 1-hydroxy-2-methyl-6-(2-phenoxyacetamido)carbapenam-3-carboxylate [68 mg

Sources & evidence

ORD record
ord-75f9b4c77b894eb9b10b2dcd9c830864
Source dataset
uspto-grants-1984_01
Patent number
US04429128

Reaction notes

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