Water → HCID 13853701, compound

HRID 231082Notes

Reaction equation

HRID 231082 reaction equation
[C:1]([C:4]1[CH:26]=[CH:25][C:7]([O:8][CH2:9][CH2:10][CH2:11][S:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([O:23]C)=[O:22])=[CH:17][N:16]=2)(=[O:14])=[O:13])=[C:6]([CH2:27][CH2:28][CH3:29])[C:5]=1[OH:30])(=[O:3])[CH3:2].[OH-].[Na+].O>C1COCC1>[C:1]([C:4]1[CH:26]=[CH:25][C:7]([O:8][CH2:9][CH2:10][CH2:11][S:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([OH:23])=[O:22])=[CH:17][N:16]=2)(=[O:14])=[O:13])=[C:6]([CH2:27][CH2:28][CH3:29])[C:5]=1[OH:30])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 13853700HCID 13853700, compound

Product 1

HCID 13853701HCID 13853701, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound of Example 3, (570 mg, 1.31 mmoles) was dissolved in THF (6 ml) to which was added 1N NaOH (3 ml) and H2O (3 ml). The reaction mixture was stirred at room temperature under N2 overnight. The THF was removed in vacuo. The aqueous phase was washed with CHCl3. Then the aqueous phase was acidified with concentrated HCl until slightly acid (pH about 5-6). The resulting beige solid was filtered, taken up in CHCl3 (about 500 ml), and the organic solvent was dried and concentrated. The residue was triturated with ether and filtered to afford the title compound, m.p. 177°-179°.

Workup

  1. customThe THF was removed in vacuo
  2. washThe aqueous phase was washed with CHCl3
  3. filtrationThe resulting beige solid was filtered
  4. customthe organic solvent was dried
  5. concentrationconcentrated
  6. customThe residue was triturated with ether
  7. filtrationfiltered

Sources & evidence

ORD record
ord-894b93ad478541749c9543da87222eaf
Source dataset
uspto-grants-1989_07
Patent number
US04845108

Reaction notes

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