Hydrochloric Acid → HCID 362692, compound

HRID 2393103Notes

Reaction equation

HRID 2393103 reaction equation
C[O:2][C:3](=[O:23])[C@H:4]([NH:11][S:12]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)(=[O:14])=[O:13])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[OH-].[Na+].Cl>C(O)C>[CH3:22][O:21][C:18]1[CH:17]=[CH:16][C:15]([S:12]([NH:11][C@H:4]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:3]([OH:23])=[O:2])(=[O:14])=[O:13])=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 1480220HCID 1480220, compound

Product 1

HCID 362692HCID 362692, compoundYield 98.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 3 mmol of 2(R)-[(4-methoxybenzenesulfonyl)amino]-2-phenyl acetic acid methyl ester in 15 mL of ethanol is added 5 mL of aqueous 2.5M sodium hydroxide. The solid suspension dissolved, and is allowed to stir, stoppered, at ambient temperature overnight. The resulting suspension is acidified with aqueous 10% HCl and extracted with ethyl acetate, adding brine to facilitate phase separation. The organic phase is washed with water and with brine and dried over sodium sulfate. It is concentrated to afford 0.95 g (quantitative yield) of a white solid.

Workup

  1. dissolutionThe solid suspension dissolved
  2. extractionextracted with ethyl acetate
  3. additionadding brine
  4. customphase separation
  5. washThe organic phase is washed with water and with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationIt is concentrated

Sources & evidence

ORD record
ord-56226fef7faf4e7197a11a3940791a19
Source dataset
uspto-grants-1998_09
Patent number
US05804593

Reaction notes

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