Water → HCID 20155854, compound

HRID 2413482Notes

Reaction equation

HRID 2413482 reaction equation
[C:1]([C:4]1[CH:31]=[CH:30][C:7]([O:8][CH2:9][CH2:10][CH2:11][S:12]([C:15]2[CH:29]=[CH:28][C:18]([C:19]([NH:21][CH2:22][C:23](=[O:27])[O:24]CC)=[O:20])=[CH:17][CH:16]=2)(=[O:14])=[O:13])=[C:6]([CH2:32][CH2:33][CH3:34])[C:5]=1[OH:35])(=[O:3])[CH3:2].[OH-].[Na+].O>C1COCC1>[C:1]([C:4]1[CH:31]=[CH:30][C:7]([O:8][CH2:9][CH2:10][CH2:11][S:12]([C:15]2[CH:29]=[CH:28][C:18]([C:19]([NH:21][CH2:22][C:23]([OH:27])=[O:24])=[O:20])=[CH:17][CH:16]=2)(=[O:14])=[O:13])=[C:6]([CH2:32][CH2:33][CH3:34])[C:5]=1[OH:35])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 14071489HCID 14071489, compound

Product 1

HCID 20155854HCID 20155854, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound of Example 3 (430 mg, 0.851 mmoles) was taken up in a mixture of THF (10 ml), 1N NaOH (1.8 ml) and water (8.2 ml). The reaction mixture was stirred at room temperature under nitrogen for two hours. The THF was then removed in vacuo and the residue was diluted with water and filtered. The aqueous solution was acidified with dilute HCl and extracted with chloroform. The combined chloroform extracts were dried and concentrated in vacuo to afford the title compound which was recrystallized from ethyl acetate/hexane, m.p. 171°-173°.

Workup

  1. customThe THF was then removed in vacuo
  2. additionthe residue was diluted with water
  3. filtrationfiltered
  4. extractionextracted with chloroform
  5. dry with materialThe combined chloroform extracts were dried
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-782c184a1c87475e9f37a8d2aab25307
Source dataset
uspto-grants-1988_01
Patent number
US04717736

Reaction notes

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