Sodium Hydroxide → HCID 67706874, compound

HRID 266284Notes

Reaction equation

HRID 266284 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@@H:12]([CH2:27][O:28][CH:29]2[CH2:34][CH2:33][CH2:32][CH2:31][O:30]2)[C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]([O:24]CC)=[O:23])=[CH:18][CH:17]=2)=[O:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[C:22]([C:19]1[CH:20]=[CH:21][C:16]([NH:15][C:13](=[O:14])[C@@H:12]([NH:11][S:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)(=[O:10])=[O:9])[CH2:27][O:28][CH:29]2[CH2:34][CH2:33][CH2:32][CH2:31][O:30]2)=[CH:17][CH:18]=1)([OH:24])=[O:23]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67706751HCID 67706751, compound

Product 1

HCID 67706874HCID 67706874, compoundYield 77.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of (S)-2-(4-chlorobenzenesulfonylamino)-N-(4-ethoxycarbonylphenyl)-3-(tetrahydropyran-2-yloxy)propanamide (200 mg), ethanol (5 ml), and 2N NaOH (2 ml) was stirred at room temperature overnight under argon. The reaction mixture was concentrated under reduced pressure. It was repeated 3 times in order to remove ethanol completely that a small amount of purified water was added to the residue, and the whole was concentrated under reduced pressure. The residue was acidified with 1N HCl, and then extracted with ethyl acetate. The combined ethyl acetate layers were washed with saturated saline solution and dried over Na2SO4. The solvent was evaporated under reduced pressure to obtain (S)-N-(4-carboxyphenyl)-2-(4-chlorobenzenesulfonylamino)-3-(tetrahydropyran-2-yloxy)propanamide (147 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto remove ethanol completely that a small amount of purified water
  3. additionwas added to the residue
  4. concentrationthe whole was concentrated under reduced pressure
  5. extractionextracted with ethyl acetate
  6. washThe combined ethyl acetate layers were washed with saturated saline solution
  7. dry with materialdried over Na2SO4
  8. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-2a6b807fe1bc4285a55fedd9ffec4529
Source dataset
uspto-grants-1997_07
Patent number
US05650428

Reaction notes

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