Water → HCID 13853707, compound

HRID 231083Notes

Reaction equation

HRID 231083 reaction equation
[C:1]([C:4]1[CH:27]=[CH:26][C:7]([O:8][CH2:9][CH2:10][CH2:11][S:12]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][C:22]([O:24]C)=[O:23])=[CH:17][N:16]=2)(=[O:14])=[O:13])=[C:6]([CH2:28][CH2:29][CH3:30])[C:5]=1[OH:31])(=[O:3])[CH3:2].[OH-].[Na+].O>C1COCC1>[C:1]([C:4]1[CH:27]=[CH:26][C:7]([O:8][CH2:9][CH2:10][CH2:11][S:12]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][C:22]([OH:24])=[O:23])=[CH:17][N:16]=2)(=[O:14])=[O:13])=[C:6]([CH2:28][CH2:29][CH3:30])[C:5]=1[OH:31])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 13853706HCID 13853706, compound

Product 1

HCID 13853707HCID 13853707, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound of Example 8, (700 mg, 1.56 mmoles) was taken up in a mixture of THF (14 ml), 2 eq. 1N NaOH (3.3 ml) and H2O (10 ml). The reaction mixture was stirred at room temperature under N2 for 2 hours. The THF was removed in vacuo. The aqueous phase was extracted with ether, then acidified with HCl and extracted into CHCl3. The combined organic extracts were dried and concentrated. The residue was triturated with ether to afford the title compound, m.p. 154°-156°. Analysis, calculated: C, 57.92; H, 5.79; S, 7.36. Found: C, 57.93; H, 5.83; S, 7.59.

Workup

  1. customThe THF was removed in vacuo
  2. extractionThe aqueous phase was extracted with ether
  3. extractionextracted into CHCl3
  4. customThe combined organic extracts were dried
  5. concentrationconcentrated
  6. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-fc6c168bbb4c42faa988e6f291b58b5d
Source dataset
uspto-grants-1989_07
Patent number
US04845108

Reaction notes

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