Tetrahydrofuran → HCID 54316733, compound

HRID 1739587Notes

Reaction equation

HRID 1739587 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]([C:29](=[O:31])[NH2:30])[CH:12]=2)=[C:6]([O:32][CH3:33])[CH:5]=1.O1CCCC1.O.[OH-].[Li+]>O>[C:29]([N:13]1[C:14]2[C:19](=[CH:18][C:17]([NH:20][C:21]([O:23][CH:24]3[CH2:25][CH2:26][CH2:27][CH2:28]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)(=[O:31])[NH2:30]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 54184297HCID 54184297, compound

Product 1

HCID 54316733HCID 54316733, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 4-[1-carbamoyl-5-(cyclopentyloxycarbonyl)amino-1H-indol-3-ylmethyl]-3-methoxy-benzoic acid methylester (1.15 grams, 2.47 mmol) in a 6:1 ratio tetrahydrofuran:water (70 mL) was added lithium hydroxide monohydrate (0.21 grams, 4.94 mmol) and the resulting solution was stirred, at room temperature, for 46 hours. The reaction mixture was concentrated in vacuo to a volume of 15 mL, then diluted with water (300 mL). The aqueous solution was acidified by addition of 1 M hydrochloric acid (aq), and the resulting precipitate was collected via filtration to give 4-[1-carbamoyl-5-(cyclopentyloxycarbonyl)amino-1H-indol-3-ylmethyl]-3-methoxy-benzoic acid (1.04 grams, 93% yield).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo to a volume of 15 mL
  2. additiondiluted with water (300 mL)
  3. additionThe aqueous solution was acidified by addition of 1 M hydrochloric acid (aq)
  4. filtrationthe resulting precipitate was collected via filtration

Sources & evidence

ORD record
ord-8f9966fc02414766b47d104a1d4bd8f5
Source dataset
uspto-grants-1999_10
Patent number
US05965745

Reaction notes

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