Water → 1-Benzyl-5-(3-tert-butoxycarbonylaminomethylphenyl)-7-chloro-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetic acid

HRID 275831Notes

Reaction equation

HRID 275831 reaction equation
[CH2:1]([NH:8][C:9]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:10]=1[CH:11]([OH:27])[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH2:33].[OH-:34].[Na+]>C(OC(=O)C)C>[CH2:1]([N:8]1[C:9]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:10]=2[CH:11]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH:13]=2)[O:27][CH:10]([CH2:9][C:31]([OH:34])=[O:33])[C:11]1=[O:27])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 543305022-Benzylamino-5-chloro-alpha-(3-tert-butoxycarbonylaminomethylphenyl)benzyl alcohol

Product 1

HCID 183153211-Benzyl-5-(3-tert-butoxycarbonylaminomethylphenyl)-7-chloro-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetic acid

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of 2-benzylamino-5-chloro-α-(3-tert-butoxycarbonylaminomethylphenyl)benzyl alcohol (0.91 g) in acetic acid ethyl ester (10 ml) were added water (4 ml) and a 1N aqueous solution of sodium hydroxide (3 ml). To the mixture was added monoethyl fumarate ester chloride (330 mg), which was stirred for one hour under ice-cooling. To the mixture was added acetic acid ethyl ester (30 ml). The organic layer was washed with water and dried over anhydrous MgSO41 followed by distilling off the solvent. The residue was dissolved in ethanol (10 mL), to which was added potassium carbonate (400 mg). The mixture was stirred overnight at room temperature. Insolubles were filtered off, and the solvent was distilled off. The residue was purified by means of a silica gel column chromatography to give ethyl ester of 1-benzyl-5-(3-tert-butoxycarbonylaminomethylphenyl)-7-chloro-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetic acid (1.06 g).

Workup

  1. temperaturecooling
  2. washThe organic layer was washed with water
  3. customdried over anhydrous MgSO41
  4. distillationby distilling off the solvent
  5. dissolutionThe residue was dissolved in ethanol (10 mL), to which
  6. additionwas added potassium carbonate (400 mg)
  7. stirringThe mixture was stirred overnight at room temperature
  8. filtrationInsolubles were filtered off
  9. distillationthe solvent was distilled off
  10. customThe residue was purified by means of a silica gel column chromatography

Sources & evidence

ORD record
ord-e660761dfded4330889fd11ee1f0b43c
Source dataset
uspto-grants-2002_03
Patent number
US06352982B1

Reaction notes

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