p-Toluenesulfonic acid monohydrate → HCID 53982694, compound

HRID 1488950Notes

Reaction equation

HRID 1488950 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])[CH:9]([CH:16]([OH:20])[C:17]([OH:19])=[O:18])[O:8][CH:7]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[Cl:27])[C:6]=2[CH:28]=1.O.[C:30]1(C)C=CC(S(O)(=O)=O)=C[CH:31]=1>C(O)C>[CH2:30]([O:18][C:17](=[O:19])[CH:16]([CH:9]1[O:8][CH:7]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[Cl:27])[C:6]2[CH:28]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[N:11]([CH:12]([CH3:14])[CH3:13])[C:10]1=[O:15])[OH:20])[CH3:31]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 22903450HCID 22903450, compound

Product 1

HCID 53982694HCID 53982694, compoundYield 841.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of (3RS,5RS,αRS)-7-chloro-5-(2-chlorophenyl)-1-isopropyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-glycolic acid (0.15 g) obtained in Example 7, p-toluenesulfonic acid monohydrate (7 mg) and ethanol (20 ml) was heated for 24 hours under reflux. Ethanol was distilled off under reduced pressure. The residue was dissolved in a mixture of water (50 ml) and ethyl acetate (50 ml). The organic layer was washed with an aqueous solution of sodium hydrogencarbonate, which was dried over anhydrous magnesium sulfate, then the solvent was was distilled off under reduced pressure to leave (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 (0.14 g) as prisms, m.p. 119°-120° C.

Workup

  1. temperaturewas heated for 24 hours
  2. temperatureunder reflux
  3. distillationEthanol was distilled off under reduced pressure
  4. dissolutionThe residue was dissolved in a mixture of water (50 ml) and ethyl acetate (50 ml)
  5. washThe organic layer was washed with an aqueous solution of sodium hydrogencarbonate, which
  6. dry with materialwas dried over anhydrous magnesium sulfate
  7. distillationthe solvent was was distilled off under reduced pressure

Sources & evidence

ORD record
ord-aada6adaa6fd43ab8823ce9b00bbadff
Source dataset
uspto-grants-1997_10
Patent number
US05677298

Reaction notes

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