Methanol → 4-(5-Cyclopentyloxycarbonylamino-1H-indol-3-ylmethyl)-3-methoxy-benzoic acid

HRID 1739583Notes

Reaction equation

HRID 1739583 reaction equation
C[O:2][C:3](=[O:31])[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)[NH:13][CH:12]=2)=[C:6]([O:29][CH3:30])[CH:5]=1.CO.O1CCCC1.O.[OH-].[Li+]>O>[CH:24]1([O:23][C:21]([NH:20][C:17]2[CH:18]=[C:19]3[C:14](=[CH:15][CH:16]=2)[NH:13][CH:12]=[C:11]3[CH2:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:31])=[O:2])=[CH:5][C:6]=2[O:29][CH3:30])=[O:22])[CH2:25][CH2:26][CH2:27][CH2:28]1

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 23365866HCID 23365866, compound

Product 1

HCID 146268444-(5-Cyclopentyloxycarbonylamino-1H-indol-3-ylmethyl)-3-methoxy-benzoic acidYield 92.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 4-[5-(cyclopentyloxycarbonyl)amino-1H-indol-3-ylmethyl]-3-methoxy-benzoic acid methylester (0.82 grams, 1.95 mmol) in a 2:2:1 ratio of methanol:tetrahydrofuran:water (30 mL) was added lithium hydroxide monohydrate (0.41 grams, 0.73 mmol). The resulting solution was stirred for 12 hours at room temperature. The solution was concentrated, and the crude product treated with 1 hydrochloric acid (aq). The product was collected via filtration. Chromatography on silica gel (1:1 hexanes:ethyl acetate→5% methanol:methylene chloride) gave 4-[5-(cyclopentyloxycarbonyl)amino-1H-indol-3-ylmethyl]-3-methoxy-benzoic acid (0.735 grams, 92 yield).

Workup

  1. concentrationThe solution was concentrated
  2. additionthe crude product treated with 1 hydrochloric acid (aq)
  3. filtrationThe product was collected via filtration

Sources & evidence

ORD record
ord-d59adf0f02724cc588e8438d1a33877b
Source dataset
uspto-grants-1999_10
Patent number
US05965745

Reaction notes

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