Hydrochloric Acid → HCID 14882511, compound

HRID 330156Notes

Reaction equation

HRID 330156 reaction equation
O.[OH-].[Li+].[CH2:4]([NH:7][C:8](/[CH:10]=[CH:11]/[C:12]1[CH:20]=[C:19]2[C:15]([CH:16]=[CH:17][N:18]2[CH2:21][C:22]2[CH:31]=[CH:30][C:25]([C:26]([O:28]C)=[O:27])=[CH:24][C:23]=2[O:32][CH3:33])=[CH:14][CH:13]=1)=[O:9])[CH2:5][CH3:6].Cl>O.CO.O1CCCC1>[CH2:4]([NH:7][C:8](/[CH:10]=[CH:11]/[C:12]1[CH:20]=[C:19]2[C:15]([CH:16]=[CH:17][N:18]2[CH2:21][C:22]2[CH:31]=[CH:30][C:25]([C:26]([OH:28])=[O:27])=[CH:24][C:23]=2[O:32][CH3:33])=[CH:14][CH:13]=1)=[O:9])[CH2:5][CH3:6]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 19870592HCID 19870592, compound

Product 1

HCID 14882511HCID 14882511, compoundYield 59.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of lithium hydroxide monohydrate (0.42 g) in water (5 ml) was added to a stirred solution of methyl E-4-[6-[2-(propylcarbamoyl)vinyl]-indol-1-ylmethyl]-3-methoxybenzoate (1 g) in methanol (20 ml) and tetrahydrofuran (5 ml) under an atmosphere of nitrogen. The mixture was stirred for 20 hr, diluted with water (20 ml), and acidified to pH 4 with 6M hydrochloric acid. The white precipitate which formed was isolated by filtration, washed with water, and crystallized from hot methanol (cooling the crystallizing solution to -20°) to give the title compound (0.572 g). The mother liquor, after addition of water, yielded an additional crop of the title compound (0.255 g, 84% combined yield) as a white solid; mp 210°-212°.

Workup

  1. customThe white precipitate which formed
  2. customwas isolated by filtration
  3. washwashed with water
  4. customcrystallized from hot methanol (
  5. temperaturecooling the crystallizing solution to -20°)

Sources & evidence

ORD record
ord-93d7e04e49c64198a31b7aec0dcbaf59
Source dataset
uspto-grants-1990_01
Patent number
US04894386

Reaction notes

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