Pyridine → HCID 70508183, compound

HRID 2296559Notes

Reaction equation

HRID 2296559 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.N1C=CC=CC=1.[C:57](OC(=O)C)(=[O:59])[CH3:58]>CN(C)C1C=CN=CC=1.C1(C)C=CC=CC=1.C(OCC)(=O)C.C(Cl)(Cl)Cl>[C:57]([O: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]([CH3:14])([CH3:15])[CH3:16])=[O:8])[CH:2]1[CH3:1])(=[O:59])[CH3:58]

Participants

9

Reactant 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 169536Tetrabutylammonium borohydrideHCID 70507356HCID 70507356, compound

Product 1

HCID 70508183HCID 70508183, compoundYield 6.8%

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent2×HCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-10 °C

Procedure

By the procedure of Example 18, pivaloyloxymethyl 2-methyl-1-oxo-6-(2-phenoxyacetamido)carbapenam-3-carboxylate (135 mg., 0.3 mmoles) was reduced with tetrabutylammonium borohydride and the isolation taken to the stage at which a washed, dried and filtered solution of pivaloyloxymethyl 1-hydroxy-2-methyl-6-(2-phenoxyacetamido)carbapenam-3-carboxylate in methylene chloride was in hand. This solution was cooled to -10° C. Pyridine (24 mg., 0.3 mmoles), acetic anhydride (31 mg., 0.3 mmoles) and 4-dimethylaminopyridine (4 mg., 0.3 mmoles) were added in sequence. After stirring for 1 hour at -10° C., tlc (4:1 chlorform:ethyl acetate) indicated complete acetylation. The reaction mixture was diluted with toluene and stripped to dryness in vacuo, with toluene chases. Chromatography on silica gel (20:1 methylene chloride:ethyl acetate) gave pivaloyloxymethyl 1-acetoxy-2-methyl-6-(2-phenoxyacetamido)carbapenam-3-carboxylate [10 mg.; Rf 0.36 (4:1 chloroform:ethyl acetate); ir (CH2Cl2) 1780, 1750, 1685 cm- ].

Workup

  1. customdried
  2. filtrationfiltered solution of pivaloyloxymethyl 1-hydroxy-2-methyl-6-(2-phenoxyacetamido)carbapenam-3-carboxylate in methylene chloride

Sources & evidence

ORD record
ord-9347c81b8a284f6f84c75c7d2c15d265
Source dataset
uspto-grants-1984_01
Patent number
US04429128

Reaction notes

Loading…