Hydrochloric Acid → N-(cis-7-chloro-1-isopropyl-5-phenyl-1,2,3,5-tetrahydro-2-oxo-4,1-benzoxazepin-3-ylacetyl)glycine

HRID 1785Notes

Reaction equation

HRID 1785 reaction equation
C([O:3][C:4](=[O:32])[CH2:5][NH:6][C:7](=[O:31])[CH2:8][C@H:9]1[O:15][C@@H:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:13]2[CH:22]=[C:23]([Cl:26])[CH:24]=[CH:25][C:12]=2[N:11]([CH:27]([CH3:29])[CH3:28])[C:10]1=[O:30])C.C(=O)([O-])[O-].[K+].[K+].Cl>CO.O>[Cl:26][C:23]1[CH:24]=[CH:25][C:12]2[N:11]([CH:27]([CH3:28])[CH3:29])[C:10](=[O:30])[C@@H:9]([CH2:8][C:7]([NH:6][CH2:5][C:4]([OH:32])=[O:3])=[O:31])[O:15][C@@H:14]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:13]=2[CH:22]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 69946886N-[cis-7-chloro-1-isopropyl-5-phenyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepin-3-ylacetyl]glycine ethyl ester

Product 1

HCID 69947625N-(cis-7-chloro-1-isopropyl-5-phenyl-1,2,3,5-tetrahydro-2-oxo-4,1-benzoxazepin-3-ylacetyl)glycineYield 64.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

In a mixture of 2 ml of methanol and 1 ml of water was suspended 48 mg of N-(trans-7-chloro-1-isopropyl-5-phenyl-1,2,3,5-tetrahydro-2-oxo-4,1-benzoxazepin-3-ylacetyl)glycine ethyl ester obtained in Example 55. To the suspension was added 0.1 g of potassium carbonate. The mixture was stirred for 6 hours at room temperature. The reaction mixture was adjusted to pH 4 with dilute hydrochloric acid, which was subjected to extraction with ethyl acetate. The organic layer was washed with water and dried, then the solvent was distilled off under reduced pressure. Crystals obtained form the residue were recrystallized from ether and hexane to afford 29 mg of N-(cis-7-chloro-1-isopropyl-5-phenyl-1,2,3,5-tetrahydro-2-oxo-4,1-benzoxazepin-3-ylacetyl)glycine as white needles.

Workup

  1. extractionwas subjected to extraction with ethyl acetate
  2. washThe organic layer was washed with water
  3. customdried
  4. distillationthe solvent was distilled off under reduced pressure
  5. customCrystals obtained form the residue
  6. customwere recrystallized from ether and hexane

Sources & evidence

ORD record
ord-a28f563304e54fffb04c32e3c16b18c3
Source dataset
uspto-grants-1998_03
Patent number
US05726306

Reaction notes

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