trans-7-Chloro-5-(2-chlorophenyl)-1-isopropyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-crotonic acid → trans-7-Chloro-5-(2-chlorophenyl)-1-isopropyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-butyric acid

HRID 1419045Notes

Reaction equation

HRID 1419045 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH:12]([CH3:14])[CH3:13])[C:10](=[O:15])[C@@H:9]([CH2:16]/[CH:17]=[CH:18]/[C:19]([OH:21])=[O:20])[O:8][C@H:7]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[Cl:28])[C:6]=2[CH:29]=1.[H][H]>C(OCC)(=O)C.[C].[Pd]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH:12]([CH3:13])[CH3:14])[C:10](=[O:15])[C@@H:9]([CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])[O:8][C@H:7]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[Cl:28])[C:6]=2[CH:29]=1

Participants

5

Reactant 2

HCID 86752222trans-7-Chloro-5-(2-chlorophenyl)-1-isopropyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-crotonic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 69946426trans-7-Chloro-5-(2-chlorophenyl)-1-isopropyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-butyric acidYield 0.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

In ethyl acetate (20 ml) was dissolved ethyl ester of trans-7-chloro-5-(2-chlorophenyl)-1-isopropyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-crotonic acid (0:45 g). To the solution was added 10% palladium carbon (0.1 g), and the mixture was subjected to catalytic reduction at room temperatures under atmospheric pressure. The theoretical amount of hydrogen was allowed to be absorbed, then the catalyst was removed, followed by distilling off ethyl acetate under reduced pressure. The residue was crystallized from a small volume of hexane to give ethyl ester of trans-7-chloro-5-(2-chlorophenyl)-1-isopropyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-butyric acid (0.37 g) as prisms, m.p.100°-101° C.

Workup

  1. customto be absorbed
  2. customthe catalyst was removed
  3. distillationby distilling off ethyl acetate under reduced pressure
  4. customThe residue was crystallized from a small volume of hexane

Sources & evidence

ORD record
ord-26f087af6c0a4f79825c67cd3acbd53c
Source dataset
uspto-grants-1999_03
Patent number
US05885979

Reaction notes

Loading…