4-(Trifluoromethyl)benzenemethanol → HCID 86757998, compound

HRID 843750Notes

Reaction equation

HRID 843750 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][C:16]([N:18]2[CH2:23][CH2:22][CH2:21][C@@H:20]([C:24]([NH:26][C@H:27]([C:32]#[CH:33])[CH2:28][C:29]([OH:31])=[O:30])=[O:25])[CH2:19]2)=[O:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:34][C:35]([F:45])([F:44])[C:36]1[CH:43]=[CH:42][C:39]([CH2:40]O)=[CH:38][CH:37]=1.Cl.C(N=C=NCCCN(C)C)C>ClCCl>[F:34][C:35]([F:44])([F:45])[C:36]1[CH:43]=[CH:42][C:39]([CH2:40][O:30][C:29](=[O:31])[CH2:28][C@@H:27]([C:32]#[CH:33])[NH:26][C:24]([C@@H:20]2[CH2:21][CH2:22][CH2:23][N:18]([C:16](=[O:17])[CH2:15][CH2:14][CH:11]3[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:13][CH2:12]3)[CH2:19]2)=[O:25])=[CH:38][CH:37]=1

Participants

5

Reactant 3

HCID 676844-(Trifluoromethyl)benzenemethanolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86757999HCID 86757999, compound

Product 1

HCID 86757998HCID 86757998, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of N-[(R)-1-{3-(1-tert-butoxycarbonyl-4-piperidyl)propionyl}-3-piperidylcarbonyl]-3(S)ethynyl-β-alanine (0.63 g), 4-(trifluoromethyl)benzyl alcohol (0.23 ml) and N,N-dimethylaminopyridine (18 mg) in dichloromethane (7 ml) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.32 g) under stirring at 0° C. After stirring at ambient temperature for overnight, the solution was evaporated in vacuo. The residue was poured into water and extracted with ethyl acetate. The extract was washed with saturated aqueous NaHCO3 solution, water and brine, and dried over MgSO4, and evaporated in vacuo. The residue was purified by column chromatography on silica gel eluting with (CHCl3:MeOH=100:1) to give N-[(R)-1-{3-(1-tert-butoxycarbonyl-4-piperidyl)propionyl}-3-piperidylcarbonyl]-3(S)-ethynyl-β-alanine 4-trifluoromethylbenzyl ester (0.71 g) as an oil.

Workup

  1. stirringAfter stirring at ambient temperature for overnight
  2. customthe solution was evaporated in vacuo
  3. additionThe residue was poured into water
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with saturated aqueous NaHCO3 solution, water and brine
  6. dry with materialdried over MgSO4
  7. customevaporated in vacuo
  8. customThe residue was purified by column chromatography on silica gel eluting with (CHCl3:MeOH=100:1)

Sources & evidence

ORD record
ord-5c8827fd884140c5b66cf0e35f11b724
Source dataset
uspto-grants-2002_04
Patent number
US06380215B1

Reaction notes

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