Hydrochloric Acid → HCID 14722388, compound

HRID 1031718Notes

Reaction equation

HRID 1031718 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[C:24]([O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:23][C:9]2[C:10](=[O:22])[C:11]([N:14]([CH:20]=[O:21])[CH2:15][C:16]([O:18]C)=[O:17])=[CH:12][O:13][C:8]=2[CH:7]=1)(=[O:4])=[O:3].Cl>[OH-].[Na+]>[CH3:1][S:2]([NH:5][C:6]1[C:24]([O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:23][C:9]2[C:10](=[O:22])[C:11]([N:14]([CH2:15][C:16]([OH:18])=[O:17])[CH:20]=[O:21])=[CH:12][O:13][C:8]=2[CH:7]=1)(=[O:3])=[O:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 14722348HCID 14722348, compound

Product 1

HCID 14722388HCID 14722388, compoundYield 82.6%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

In 45 ml of a 1N aqueous sodium hydroxide solution was dissolved 4.46 g of 7-methylsulfonylamino- 3-(N-formyl-N-methoxycarbonylmethylamino)-6-phenoxy-4H-1-benzopyran-4-one. The solution was stirred for 1.5 hours at 25°-30° C. The solution was then adjusted to pH 3 with 4N hydrochloric acid and extracted with two 50-ml portions of ethyl acetate. The extracts (the organic layers) were combined, washed with water and a saturated aqueous sodium chloride solution in this order, and dried with anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was mixed with diethyl ether. The resulting crystal was collected by filtration to obtain 3.57 g (yield: 82.6%) of 7-methylsulfonylamino-3-(N-carboxymethyl-N-formylamino)-6-phenoxy-4H-1-benzopyran-4-one having a melting point of 98°-100° C.

Workup

  1. extractionextracted with two 50-ml portions of ethyl acetate
  2. washwashed with water
  3. dry with materiala saturated aqueous sodium chloride solution in this order, and dried with anhydrous magnesium sulfate
  4. customThe solvent was removed by distillation under reduced pressure
  5. additionThe residue was mixed with diethyl ether
  6. filtrationThe resulting crystal was collected by filtration

Sources & evidence

ORD record
ord-79e522e975d4441a8328444c98cb8352
Source dataset
uspto-grants-1990_09
Patent number
US04954518

Reaction notes

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