Hydrochloric Acid → HCID 54303394, compound

HRID 1739588Notes

Reaction equation

HRID 1739588 reaction equation
C[O:2][C:3](=[O:34])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([NH:20][C:21]([O:23][CH:24]4[CH2:28][CH2:27][CH2:26][CH2:25]4)=[O:22])[CH:18]=3)[N:13]([CH:29]([F:31])[F:30])[CH:12]=2)=[C:6]([O:32][CH3:33])[CH:5]=1.O1CCCC1.CO.O.[OH-].[Li+].Cl>O>[F:31][CH:29]([F:30])[N:13]1[C:14]2[C:19](=[CH:18][C:17]([NH:20][C:21]([O:23][CH:24]3[CH2:28][CH2:27][CH2:26][CH2:25]3)=[O:22])=[CH:16][CH:15]=2)[C:11]([CH2:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:34])=[O:2])=[CH:5][C:6]=2[O:32][CH3:33])=[CH:12]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 21899815MeOH tetrahydrofuranHCID 53958176HCID 53958176, compound

Product 1

HCID 54303394HCID 54303394, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 4-[1-difluoromethyl-5-(cyclopentyloxycarbonyl)amino-1H-indol-3-ylmethyl]-3-methoxy-benzoic acid methylester (0.40 grams, 0.84 mmol) in a 5:5:2 ratio of methanol tetrahydrofuran:water (24 mL) was added lithium hydroxide monohydrate (0.18 grams, 4.18 mmol). The resulting solution was stirred for 24 hours at room temperature. The reaction mixture was then acidified with 1 M hydrochloric acid (aq) and extracted with ethyl acetate. The combined organics were washed with water and brine, then dried over sodium sulfate. Concentration in vacuo gave 4-[1-difluoromethyl-5-(cyclopentyloxycarbonyl)amino-1H-indol-3-ylmethyl]-3-methoxy-benzoic acid as a white solid (0.40 grams, 1005 yield). An analytical sample was attained by recrystallization from ethyl acetate/hexanes.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organics were washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationConcentration in vacuo
  5. customgave

Sources & evidence

ORD record
ord-14c403f9664b42c8bbdb88cc034bc6ee
Source dataset
uspto-grants-1999_10
Patent number
US05965745

Reaction notes

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