Hydrochloric Acid → cis-1-Benzyl-2-oxo-5-phenyl-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-propionic acid

HRID 1779Notes

Reaction equation

HRID 1779 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH2:12][C:13]3[CH:18]=[CH:17][C:16](OC)=[CH:15][C:14]=3OC)[C:10](=[O:23])[C@@H:9](CC(O)=O)[O:8][C@H:7]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3Cl)[C:6]=2[CH:35]=1.[OH-:36].[Na+].Cl>CO>[CH2:12]([N:11]1[C:5]2[CH:4]=[CH:3][CH:2]=[CH:35][C:6]=2[C@H:7]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[O:8][C@H:9]([CH2:5][CH2:6][C:7]([OH:8])=[O:36])[C:10]1=[O:23])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69946224trans-7-Chloro-5-(2-chlorophenyl)-1-(2,4-dimethoxybenzyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetic acid

Product 1

HCID 69945752cis-1-Benzyl-2-oxo-5-phenyl-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-propionic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 20 ml of methanol was dissolved 0.5 g of ethyl ester of cis-1-benzyl-2-oxo-5-phenyl-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-propionic acid obtained in Example 8. To the solution was added 7 ml of 1N sodium hydroxide, and the mixture was stirred for 30 minutes at room temperature. The reaction mixture was acidified with 100 ml of 1N hydrochloric acid, which was subjected to extraction with 150 ml of ethyl acetate. The ethyl acetate layer was washed with water and dried over anhydrous magnesium sulfate. Then the solvent was distilled off under reduced pressure to leave 0.46 g of cis-1-benzyl-2-oxo-5-phenyl-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-propionic acid as plates, m.p. 112°-114° C.

Workup

  1. extractionwas subjected to extraction with 150 ml of ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThen the solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-b5522d18fb004b81842dc376c274bba5
Source dataset
uspto-grants-1998_03
Patent number
US05726306

Reaction notes

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