1-{[1-(4-Trifluoromethyl-benzyloxy)-naphthalene-2-carbonyl]-amino}-cyclopent-3-enecarboxylic acid methyl ester → 1-{[1-(4-Trifluoromethyl-benzyl-oxy)-naphthalene-2-carbonyl]-amino}-cyclopent-3-enecarboxylic acid

HRID 1039113Notes

Reaction equation

HRID 1039113 reaction equation
C[O:2][C:3]([C:5]1([NH:10][C:11]([C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]=2[O:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=2)=[O:12])[CH2:9][CH:8]=[CH:7][CH2:6]1)=[O:4]>C1COCC1.[OH-].[Li+].CO>[F:32][C:31]([F:33])([F:34])[C:28]1[CH:27]=[CH:26][C:25]([CH2:24][O:23][C:14]2[C:15]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:21]=[CH:22][C:13]=2[C:11]([NH:10][C:5]2([C:3]([OH:4])=[O:2])[CH2:6][CH:7]=[CH:8][CH2:9]2)=[O:12])=[CH:30][CH:29]=1

Participants

5

Reactant 1

HCID 688420571-{[1-(4-Trifluoromethyl-benzyloxy)-naphthalene-2-carbonyl]-amino}-cyclopent-3-enecarboxylic acid methyl ester

Product 1

HCID 247696161-{[1-(4-Trifluoromethyl-benzyl-oxy)-naphthalene-2-carbonyl]-amino}-cyclopent-3-enecarboxylic acidYield 65.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3939Lithium HydroxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

316 mg 1-{[1-(4-trifluoromethyl-benzyloxy)-naphthalene-2-carbonyl]-amino}-cyclopent-3-enecarboxylic acid methyl ester in 9 ml THF, 1.6 ml of 2 M lithium hydroxide and 18 ml methanol were reacted at room temperature for 8 h. The organic solvents were then removed in vacuo, and the residue was acidified with 2 M hydrochloric acid and extracted with ethyl acetate twice. The combined organic layers were dried over magnesium sulphate, and concentrated to yield 200 mg of 1-{[1-(4-trifluoromethyl-benzyl-oxy)-naphthalene-2-carbonyl]-amino}-cyclopent-3-enecarboxylic acid.

Workup

  1. customThe organic solvents were then removed in vacuo
  2. extractionextracted with ethyl acetate twice
  3. dry with materialThe combined organic layers were dried over magnesium sulphate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d1de8ac6191841cc99c8a4d4db6ff1e8
Source dataset
uspto-grants-2013_10
Patent number
US08552033B2

Reaction notes

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