Methanol → t-butyl 4-[6-(N-cyclopentylmethylcarbamoyl)-3-(2-carboxypropyl)indol-1-ylmethyl]-3-methoxybenzoate

HRID 1198970Notes

Reaction equation

HRID 1198970 reaction equation
[CH:1]1([CH2:6][NH:7][C:8]([C:10]2[CH:18]=[C:17]3[C:13]([C:14]([CH2:35][CH:36]([C:38]([O:40]CC)=[O:39])[CH3:37])=[CH:15][N:16]3[CH2:19][C:20]3[CH:32]=[CH:31][C:23]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[CH:22][C:21]=3[O:33][CH3:34])=[CH:12][CH:11]=2)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.CO.O.O.[OH-].[Li+]>O1CCCC1>[CH:1]1([CH2:6][NH:7][C:8]([C:10]2[CH:18]=[C:17]3[C:13]([C:14]([CH2:35][CH:36]([C:38]([OH:40])=[O:39])[CH3:37])=[CH:15][N:16]3[CH2:19][C:20]3[CH:32]=[CH:31][C:23]([C:24]([O:26][C:27]([CH3:28])([CH3:30])[CH3:29])=[O:25])=[CH:22][C:21]=3[O:33][CH3:34])=[CH:12][CH:11]=2)=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 15013787t-butyl 4-[6-(N-cyclopentylmethylcarbamoyl)-3-(2-ethoxycarbonylpropyl)indol-1-ylmethyl]-3-methoxybenzoate

Product 1

HCID 15013788t-butyl 4-[6-(N-cyclopentylmethylcarbamoyl)-3-(2-carboxypropyl)indol-1-ylmethyl]-3-methoxybenzoateYield 95.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of t-butyl 4-[6-(N-cyclopentylmethylcarbamoyl)-3-(2-ethoxycarbonylpropyl)indol-1-ylmethyl]-3-methoxybenzoate (0.75 g) in a mixture of tetrahydrofuran (3.5 ml), methanol (3.5 ml), and water (1.3 ml) was treated with lithium hydroxide monohydrate (0.33 g). The mixture was stirred at 30° for 6 hours and then concentrated to remove the organic solvents. The residue was dissolved in water, and the solution was acidified with 10% (v/v) hydrochloric acid. The precipitate which formed was collected by filtration and dried to give t-butyl 4-[6-(N-cyclopentylmethylcarbamoyl)-3-(2-carboxypropyl)indol-1-ylmethyl]-3-methoxybenzoate (0.68 g, 95%) as a white powder; mp 195°-197°; partial NMR (80 MHz, CDCl3): 2.55-3.24(m, 3H, CH2CHCH3), 3.38(t, 2H, NHCH2), 3.91(s, 3H, OCH3), 5.24(s, 2H, NCH2), 6.17(br t, 1H, NH), 6.61(d, 1H, Ar), 7.04(s, 1H, H2 -indole), 7.85(br s, 1H, H7 -indole).

Workup

  1. concentrationconcentrated
  2. customto remove the organic solvents
  3. dissolutionThe residue was dissolved in water
  4. customThe precipitate which formed
  5. filtrationwas collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-dc2f375e06c7410bb0d6978301936ffa
Source dataset
uspto-grants-1990_02
Patent number
US04898863

Reaction notes

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