Methanol → HCID 54439973, compound

HRID 2371792Notes

Reaction equation

HRID 2371792 reaction equation
[CH:1]1([CH2:6][C:7]([NH:9][C:10]2[CH:19]=[C:18]3[C:13]([CH:14]=[CH:15][CH:16]=[C:17]3[CH2:20][C:21]3[CH:30]=[CH:29][C:24]([C:25]([O:27]C)=[O:26])=[CH:23][C:22]=3[O:31][CH3:32])=[CH:12][CH:11]=2)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.CO.O1CCCC1.O.[OH-].[Li+]>O>[CH:1]1([CH2:6][C:7]([NH:9][C:10]2[CH:19]=[C:18]3[C:13]([CH:14]=[CH:15][CH:16]=[C:17]3[CH2:20][C:21]3[CH:30]=[CH:29][C:24]([C:25]([OH:27])=[O:26])=[CH:23][C:22]=3[O:31][CH3:32])=[CH:12][CH:11]=2)=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 21570391HCID 21570391, compound

Product 1

HCID 54439973HCID 54439973, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of methyl 4-[7-(cyclopentyl acetamido)naphth-1-ylmethyl]-3-methoxybenzoate (660 mg), methanol (23 ml) and tetrahydrofuran (23 ml) was added a solution of lithium hydroxide monohydrate (321 mg) in water (7.7 ml). Nitrogen was bubbled through the mixture for 30 seconds before it was stoppered and stirred for 72 h. The reaction mixture was evaporated and the residue taken up in 75 ml of 1:9 tetrahydrofuran:ethyl acetate and acidified with 3 ml of 6N HCl. The organic layer was washed (water, brine), dried (MgSO4) and evaporated. Recrystallization of the resulting solid from 1:9 methanol:methylene chloride and petroleum ether gave the title compound as a colorless solid (517 mg, 81%); mp 248.0°-250.0° C.

Workup

  1. customNitrogen was bubbled through the mixture for 30 seconds before it
  2. customThe reaction mixture was evaporated
  3. washThe organic layer was washed (water, brine)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customRecrystallization of the resulting solid from 1:9 methanol

Sources & evidence

ORD record
ord-437914e39081474ba7ed1a6e53b905c3
Source dataset
uspto-grants-1992_03
Patent number
US05095038

Reaction notes

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