Sodium Hydroxide → HCID 53761674, compound

HRID 248448Notes

Reaction equation

HRID 248448 reaction equation
[C:1]([CH2:5][CH2:6][C:7]([NH:9][CH2:10][C:11]1[CH:15]=[C:14]([C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)[NH:13][C:12]=1[C:21]1[S:22][CH:23]=[CH:24][CH:25]=1)=[O:8])([O:3]C)=[O:2].[OH-].[Na+]>CO>[C:1]([CH2:5][CH2:6][C:7]([NH:9][CH2:10][C:11]1[CH:15]=[C:14]([C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)[NH:13][C:12]=1[C:21]1[S:22][CH:23]=[CH:24][CH:25]=1)=[O:8])([OH:3])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54215536HCID 54215536, compound

Product 1

HCID 53761674HCID 53761674, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of compound XXVI (200 mg, 0.53 mmol), 0.6N aqueous sodium hydroxide (1.34 ml, 0.80 mmol) and 4 ml of methyl alcohol was stirred at room temperature for 16 hours. The reaction mixture was poured onto 15 ml of ice water and was washed with diethyl ether. The aqueous layer was acidified with 1N aqueous hydrochloric acid to pH 4.0, then saturated with sodium chloride. The saturated solution then was extracted four times with 5 ml portions of ethyl acetate. The combined organic extracts were washed with the 5 ml portions of water, dried over anhydrous magnesium sulfate, then filtered. Evaporation of solvent in vacuo gave a crude acid that was then purified on 20 g of silica gel. Elution with ethyl acetate:acetic acid, 95:5, provided 121 mg (63%) of acid (XXVII), having Rf :0.28 (ethyl acetate:acetic acid, 95:5).

Workup

  1. washwas washed with diethyl ether
  2. extractionThe saturated solution then was extracted four times with 5 ml portions of ethyl acetate
  3. washThe combined organic extracts were washed with the 5 ml portions of water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customEvaporation of solvent in vacuo
  7. customgave a crude acid that
  8. customwas then purified on 20 g of silica gel
  9. washElution with ethyl acetate

Sources & evidence

ORD record
ord-94004c32897c417588d2ef270c72cf5f
Source dataset
uspto-grants-1993_05
Patent number
US05210217

Reaction notes

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