Methanol → HCID 14882657, compound

HRID 330194Notes

Reaction equation

HRID 330194 reaction equation
[CH2:1]([NH:5][C:6]([CH2:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH3:18])[CH:13]=[C:12]2[CH2:19][C:20]1[CH:29]=[CH:28][C:23]([C:24]([O:26]C)=[O:25])=[CH:22][C:21]=1[O:30][CH3:31])=[O:7])[CH2:2][CH2:3][CH3:4].CO.O1CCCC1.O.[OH-].[Li+]>O>[CH2:1]([NH:5][C:6]([CH2:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH3:18])[CH:13]=[C:12]2[CH2:19][C:20]1[CH:29]=[CH:28][C:23]([C:24]([OH:26])=[O:25])=[CH:22][C:21]=1[O:30][CH3:31])=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 19870596HCID 19870596, compound

Product 1

HCID 14882657HCID 14882657, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of methyl 4-[5-(butylcarbamoyl)methyl-1-methylindol-3-ylmethyl]-3-methoxybenzoate (0.23 g) in a combination of methanol (2.5 ml), tetrahydrofuran (2.5 ml), and water (1.5 ml) was treated with lithium hydroxide monohydrate (0.14 g). The mixture was stirred for 18 hr and the organic solvents evaporated. The resultant aqueous solution was acidified with 10% (v/v) hydrochloric acid. The ivory precipitate which formed was collected by filtration, washed with water, and dried under vacuum to give the title compound (0.21 g, 94%) as a pale pink powder: mp 92°-95°.

Workup

  1. customthe organic solvents evaporated
  2. customThe ivory precipitate which formed
  3. filtrationwas collected by filtration
  4. washwashed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-f7bdf17d51784d3a8c3e2a5ea7487b34
Source dataset
uspto-grants-1990_01
Patent number
US04894386

Reaction notes

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