Hydrochloric Acid → HCID 22903450, compound

HRID 1488948Notes

Reaction equation

HRID 1488948 reaction equation
C([O:3][C:4](=[O:30])[CH:5]([CH:7]1[O:13][CH:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[Cl:20])[C:11]2[CH:21]=[C:22]([Cl:25])[CH:23]=[CH:24][C:10]=2[N:9]([CH:26]([CH3:28])[CH3:27])[C:8]1=[O:29])[OH:6])C.[OH-].[Na+].Cl>C(O)C>[Cl:25][C:22]1[CH:23]=[CH:24][C:10]2[N:9]([CH:26]([CH3:28])[CH3:27])[C:8](=[O:29])[CH:7]([CH:5]([OH:6])[C:4]([OH:30])=[O:3])[O:13][CH:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[Cl:20])[C:11]=2[CH:21]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 53982694HCID 53982694, compound2×

Product 1

HCID 22903450HCID 22903450, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture (4.5 g) of (3RS,5RS,αRS)-7-chloro-5-(2-chlorophenyl)-1-isopropyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-glycolic acid ethyl ester and (3RS,5SR,αRS)-7-chloro-5-(2-chlorophenyl)-1-isopropyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-glycolic acid ethyl ester obtained in Example 2 was dissolved in ethanol (50 ml). To the solution was added 1N sodium hydroxide (30 ml), and mixture was stirred for 30 minutes at room temperature. To the resultant mixture was added 1N hydrochloric acid (100 ml) to make the solution acid, which was extracted with ethyl acetate (200 ml). The extract solution was washed with water, dried over anhydrous magnesium sulfate, then the solvent was distilled off under reduced pressure. The residue was crystallized from hexane-ethyl acetate to give a mixture (3.3 g) of (3RS,5RS,αRS)-7-chloro-5-(2-chlorophenyl)-1-isopropyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-glycolic acid and (3RS,5SR,αRS)-7-chloro-5-(2-chlorophenyl)-1-isopropyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-glycolic acid. This mixture was recrystallized twice from hexane-ethanol to give (3RS,5SR,αRS)-7-chloro-5-(2-chlorophenyl)-1-isopropyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-glycolic acid (0.94 g) as plates, m.p. 226°-230° C. (decomp.).

Workup

  1. extractionwas extracted with ethyl acetate (200 ml)
  2. washThe extract solution was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was crystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-d8fd76af7f4240fdab55e4178640cae4
Source dataset
uspto-grants-1997_10
Patent number
US05677298

Reaction notes

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