Trifluoroacetic acid → HCID 86603622, compound

HRID 226314Notes

Reaction equation

HRID 226314 reaction equation
C(OC([N:8]([C@@H:22]1[CH2:26][CH2:25][N:24]([CH2:27][C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=2)[CH2:23]1)[C:9]1[N:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:11][CH:10]=1)=O)(C)(C)C.C1(OC)C=CC=CC=1.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>ClCCl.CCOC(C)=O.O>[CH3:35][O:34][C:31]1[CH:32]=[CH:33][C:28]([CH2:27][N:24]2[CH2:25][CH2:26][C@@H:22]([NH:8][C:9]3[N:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:11][CH:10]=3)[CH2:23]2)=[CH:29][CH:30]=1

Participants

8

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 516892Sodium BicarbonateHCID 86603621HCID 86603621, compound

Product 1

HCID 86603622HCID 86603622, compoundYield 103.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

To an ice-cooled solution of ethyl (2E)-3-(6-{(tert-butoxycarbonyl)[(3R)-1-(4-methoxybenzyl)-3-pyrrolidinyl]amino}-3-pyridyl)acrylate (360 mg) in dichloromethane (2 ml) was added anisole (11.0 ml) and TFA (2.0 ml), the mixture was stirred at 20° C. for 1 hour. The mixed solution was poured into a mixture of water (20 ml) and AcOEt (20 ml). The pH of the aqueous layer was adjusted to ca. 9 with NaHCO3. The organic layer was separated, washed with brine, dried over sodium sulfate and evaporated under reduced pressure to give ethyl (2E)-3-(6-{[(3R)-1-(4-methoxybenzyl)-3-pyrrolidinyl]amino}-3-pyridyl)acrylate as syrup (295 mg).

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-f0b7096a52394a33a4b4590a29d784b0
Source dataset
uspto-grants-2009_07
Patent number
US07557127B2

Reaction notes

Loading…