Dichloromethane → HCID 70507342, compound

HRID 1702725Notes

Reaction equation

HRID 1702725 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:43])[CH:19]([NH:20][C:21](=[O:42])[CH:22]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[NH:23][C:24]([N:26]3[CH2:31][CH2:30][N:29]([CH2:32][CH3:33])[C:28](=[O:34])[C:27]3=[O:35])=[O:25])[C@H:4]2[C:3]1=[O:44].C(Cl)Cl.[BH4-].C([N+](CCCC)(CCCC)CCCC)CCC>C(OCC)(=O)C.C(Cl)(Cl)Cl>[OH:44][CH:3]1[C@@H:4]2[CH:19]([NH:20][C:21](=[O:42])[CH:22]([C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)[NH:23][C:24]([N:26]3[CH2:31][CH2:30][N:29]([CH2:32][CH3:33])[C:28](=[O:34])[C:27]3=[O:35])=[O:25])[C:18](=[O:43])[N:5]2[CH:6]([C:7]([O:9][CH2:10][O:11][C:12](=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14])=[O:8])[CH:2]1[CH3:1]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 169536Tetrabutylammonium borohydrideHCID 70506715HCID 70506715, compound

Product 1

HCID 70507342HCID 70507342, compoundYield 15.2%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

Pivaloyloxymethyl 2-methyl-1-oxo-6-[2-phenyl-2-(4-ethyl-2,3dioxopiperazine-1-carboxamido)acetamido]carbapenam-3-carboxylate (103 mg., 0.16 mmole) in 10 ml. of methylene chloride was reacted with tetrabutylammonium borohydride (11 mg., 0.04 mmole) at -78° C. After 15 minutes tlc (ethyl acetate) indicated reduction was complete. Isolation according to Example 3, except using 1:1 chloroform:ethyl acetate as eluant in the chromatography, afforded pivaloyloxymethyl 1-hydroxy-2-methyl-6-[2-phenyl-2-(4-ethyl-2,3-dioxopiperazine-1-carboxamido)acetamido]carbapenam-3-carboxylate [15 mg., 15%; ir (CH2Cl2) 1775, 1760, 1720, 1690 cm-1 ; Rf 0.0 (ethyl acetate)].

Sources & evidence

ORD record
ord-1d31229a8461411ea86d822bd7b35c17
Source dataset
uspto-grants-1982_09
Patent number
US04348264

Reaction notes

Loading…