p-Toluenesulfonic acid monohydrate → HCID 53982694, compound

HRID 1488949Notes

Reaction equation

HRID 1488949 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 665.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of (3RS,5SR,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 (6 mg) and ethanol (20 ml) was heated for 10 hours under reflux. Ethanol was distilled off under reduced pressure. To the residue were added water (50 ml) and ethyl acetate (50 ml). The organic layer was washed with an aqueous solution of sodium hydrogencarbonate, dried over anhydrous magnesium sulfate, followed by distilling off the solvent under reduced pressure to leave (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 (95 mg) as prisms, m.p. 126°-128° C.

Workup

  1. temperaturewas heated for 10 hours
  2. temperatureunder reflux
  3. distillationEthanol was distilled off under reduced pressure
  4. additionTo the residue were added water (50 ml) and ethyl acetate (50 ml)
  5. washThe organic layer was washed with an aqueous solution of sodium hydrogencarbonate
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationby distilling off the solvent under reduced pressure

Sources & evidence

ORD record
ord-9ffc42663a1f451c94456ea606f14fae
Source dataset
uspto-grants-1997_10
Patent number
US05677298

Reaction notes

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