Dichloromethane → HCID 70507910, compound

HRID 2296568Notes

Reaction equation

HRID 2296568 reaction equation
[CH3:1][CH:2]1[CH:6]([C:7]([O:9][CH2:10][C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=2)=[O:8])[N:5]2[C:21](=[O:46])[CH:22]([NH:23][C:24](=[O:45])[CH:25]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[NH:26][C:27]([N:29]3[CH2:34][CH2:33][N:32]([CH2:35][CH3:36])[C:31](=[O:37])[C:30]3=[O:38])=[O:28])[C@H:4]2[C:3]1=[O:47].C(Cl)Cl.[BH4-].C([N+](CCCC)(CCCC)CCCC)CCC>C(OCC)(=O)C>[OH:47][CH:3]1[C@@H:4]2[CH:22]([NH:23][C:24](=[O:45])[CH:25]([C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)[NH:26][C:27]([N:29]3[CH2:34][CH2:33][N:32]([CH2:35][CH3:36])[C:31](=[O:37])[C:30]3=[O:38])=[O:28])[C:21](=[O:46])[N:5]2[CH:6]([C:7]([O:9][CH2:10][C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=2)=[O:8])[CH:2]1[CH3:1]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 169536Tetrabutylammonium borohydrideHCID 70507602HCID 70507602, compound

Product 1

HCID 70507910HCID 70507910, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-Naphthylmethyl 2-methyl-1-oxo-6-[2-phenyl-2-(4-ethyl-2,3-dioxopiperazine-1-carboxamido)acetamido]carbapenam-3-carboxylate (36 mg., 0.056 mmole) in 3.6 ml. of methylene chloride at -78° C. was reduced with tetrabutylammonium borohydride (3.6 mg., 0.014 mmoles). After a 1 hour reaction time at -78° C., tlc (ethyl acetate) indicated conversion was complete. Isolation according to Example 3 (without chromatography) afforded 2-naphthylmethyl 1-hydroxy-2-methyl-6-[2-phenyl-2-(4-ethyl-2,3-dioxopiperazine-1-carboxamido)acetamido]carbapenam-3-carboxylate [36 mg.; Rf 0.13 (ethyl acetate)].

Workup

  1. customat -78° C.
  2. customAfter a 1 hour reaction time at -78° C.

Sources & evidence

ORD record
ord-3ff1037dc6884be39877787bd2e6efe4
Source dataset
uspto-grants-1984_01
Patent number
US04429128

Reaction notes

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