Tetrahydrofuran → HCID 178480528, compound

HRID 1372774Notes

Reaction equation

HRID 1372774 reaction equation
[Cl:1][C:2]1[C:3]([NH:29][C:30]([C:32]2[C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[N:34]([CH3:41])[CH:33]=2)=[O:31])=[CH:4][C:5]([F:28])=[C:6]([CH2:8][C:9]([N:11]2[CH2:15][CH2:14][CH2:13][C@H:12]2[CH2:16][O:17][CH:18]2[CH2:23][CH2:22][CH:21]([C:24]([O:26]C)=[O:25])[CH2:20][CH2:19]2)=[O:10])[CH:7]=1.C1COCC1.[OH-].[Na+]>Cl>[Cl:1][C:2]1[C:3]([NH:29][C:30]([C:32]2[C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[N:34]([CH3:41])[CH:33]=2)=[O:31])=[CH:4][C:5]([F:28])=[C:6]([CH2:8][C:9]([N:11]2[CH2:15][CH2:14][CH2:13][C@H:12]2[CH2:16][O:17][C@H:18]2[CH2:23][CH2:22][C@H:21]([C:24]([OH:26])=[O:25])[CH2:20][CH2:19]2)=[O:10])[CH:7]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 21071352HCID 21071352, compound

Product 1

HCID 178480528HCID 178480528, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To methyl 4-(1-((5-chloro-2-fluoro-4-(1-methyl-3-indolylcarbonylamino)phenyl)acetyl)-(2S)-pyrrolidinyl methoxy)-1-cyclohexanecarboxylate (556 mg, 0.953 mmol) were added THF (10 ml) and 0.25N NaOH (10 ml, 2.50 mmol). The resulting mixture was stirred at room temperature for 15 hours. The reaction mixture was poured in 1N HCl (100 ml), followed by extraction with chloroform-methanol (5:1, 2×100 ml). The extract was dried over anhydrous magnesium sulfate and distilled under reduced pressure to remove the solvent. To the residue were added chloroform and hexane. The crystals thus precipitated were collected by filtration under reduced pressure and dried under reduced pressure to give the title compound (400 mg, 74%) as a colorless solid.

Workup

  1. extractionfollowed by extraction with chloroform-methanol (5:1, 2×100 ml)
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. distillationdistilled under reduced pressure
  4. customto remove the solvent
  5. additionTo the residue were added chloroform and hexane
  6. customThe crystals thus precipitated
  7. filtrationwere collected by filtration under reduced pressure
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-c194b536bbe14a32971897ad1b63698c
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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