Methanol → HCID 14882506, compound

HRID 330141Notes

Reaction equation

HRID 330141 reaction equation
C1([N:6]([CH3:32])[C:7]([CH2:9][C:10]2[CH:18]=[C:17]3[C:13]([CH:14]=[CH:15][N:16]3[CH2:19][C:20]3[CH:29]=[CH:28][C:23]([C:24]([O:26]C)=[O:25])=[CH:22][C:21]=3[O:30][CH3:31])=[CH:12][CH:11]=2)=[O:8])CCCC1.[CH3:33]O.O1[CH2:39][CH2:38][CH2:37][CH2:36]1.O.[OH-].[Li+]>O>[CH:36]1([CH2:32][NH:6][C:7]([CH2:9][C:10]2[CH:18]=[C:17]3[C:13]([CH:14]=[CH:15][N:16]3[CH2:19][C:20]3[CH:29]=[CH:28][C:23]([C:24]([OH:26])=[O:25])=[CH:22][C:21]=3[O:30][CH3:31])=[CH:12][CH:11]=2)=[O:8])[CH2:33][CH2:39][CH2:38][CH2:37]1

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 19870629HCID 19870629, compound

Product 1

HCID 14882506HCID 14882506, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of methyl 4-[6-(N-cyclopentyl-methylcarbamoylmethyl)indol-1-ylmethyl]-3-methoxybenzoate (1.34 g) in a combination of methanol (7.5 ml), tetrahydrofuran (7.5 ml), and water (3 ml) was treated with lithium hydroxide monohydrate (0.78 g). The mixture was stirred for 6 hr and then evaporated to remove the organic solvents. The resultant aqueous solution was acidified with 10% (v/v) hydrochloric acid. The white precipitate which formed was collected by filtration, washed with water, and dried under vacuum to give the title compound (0.70 g, 54%) as a white powder; mp 188°-189°.

Workup

  1. customevaporated
  2. customto remove the organic solvents
  3. customThe white precipitate which formed
  4. filtrationwas collected by filtration
  5. washwashed with water
  6. customdried under vacuum

Sources & evidence

ORD record
ord-6abaee067a47431780ffceb6017227de
Source dataset
uspto-grants-1990_01
Patent number
US04894386

Reaction notes

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