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

HRID 1039112Notes

Reaction equation

HRID 1039112 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]1[CH:23]=[CH:22][C:6]([CH2:7][O:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[CH:11][C:10]=2[C:19](O)=[O:20])=[CH:5][CH:4]=1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.C(N(CC)C(C)C)(C)C.Cl.[CH3:58][O:59][C:60]([C:62]1([NH2:67])[CH2:66][CH:65]=[CH:64][CH2:63]1)=[O:61]>CN(C=O)C>[CH3:58][O:59][C:60]([C:62]1([NH:67][C:19]([C:10]2[CH:11]=[CH:12][C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:9]=2[O:8][CH2:7][C:6]2[CH:22]=[CH:23][C:3]([C:2]([F:1])([F:25])[F:24])=[CH:4][CH:5]=2)=[O:20])[CH2:66][CH:65]=[CH:64][CH2:63]1)=[O:61]

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531Diisopropylethylamine2×HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68840888Methyl 1-aminocyclopent-3-ene-1-carboxylate hydrochlorideHCID 688420491-(4-Trifluoromethyl-benzyloxy)-naphthalene-2-carboxylic acid

Product 1

HCID 688420571-{[1-(4-Trifluoromethyl-benzyloxy)-naphthalene-2-carbonyl]-amino}-cyclopent-3-enecarboxylic acid methyl esterYield 118%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 200 mg 1-(4-trifluoromethyl-benzyloxy)-naphthalene-2-carboxylic acid in 2 ml abs. DMF under inert atmosphere 72 mg 1-hydroxybenzotriazole, 285 mg 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride and 288 μl of N,N-diisopropylethylamine were added at 0° C. After 30 minutes at 0° C. 229 mg of 1-amino-cyclopent-3-enecarboxylic acid methyl ester hydrochloride, followed by 223 μl of N,N-diisopropylethylamine were added. After 16 h at room temperature the reaction mixture was concentrated, the residue was taken up in ethyl acetate and washed with 2 M HCl, aqueous sodium carbonate solution (10%) and brine. The organic layer was dried over magnesium sulphate and concentrated to yield 320 mg of 1-{[1-(4-trifluoromethyl-benzyloxy)-naphthalene-2-carbonyl]-amino}-cyclopent-3-enecarboxylic acid methyl ester.

Workup

  1. additionwere added
  2. concentrationAfter 16 h at room temperature the reaction mixture was concentrated
  3. washwashed with 2 M HCl, aqueous sodium carbonate solution (10%) and brine
  4. dry with materialThe organic layer was dried over magnesium sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-03d8857a216649be96d57bb350b1ef03
Source dataset
uspto-grants-2013_10
Patent number
US08552033B2

Reaction notes

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