Water → HCID 13853707, compound

HRID 979189Notes

Reaction equation

HRID 979189 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°.

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-85a08b5664854f539f0ea1ea5b995864
Source dataset
uspto-grants-1987_05
Patent number
US04666928

Reaction notes

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