Trifluoroacetic acid → (3R,4S)-1-Benzyl-4-(4-benzyloxycarbonylamino-2-fluoro-phenyl)-pyrrolidine-3-carboxylic Acid Ethyl Ester

HRID 2193545Notes

Reaction equation

HRID 2193545 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])=[CH:9][C:8]=1[F:24])[CH3:2].C(O[CH2:32][N:33]([CH2:41][Si](C)(C)C)[CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)CCCC.FC(F)(F)C(O)=O>ClCCl>[CH2:1]([O:3][C:4]([C@@H:5]1[C@@H:6]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:15])=[CH:9][C:8]=2[F:24])[CH2:41][N:33]([CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:32]1)=[O:25])[CH3:2]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10902461N-[(pentyloxy)methyl]-N-[(trimethylsilyl)-methyl]-benzenemethanamineHCID 672740363-(4-Benzyloxycarbonylamino-2-fluoro-phenyl)-acrylic Acid Ethyl Ester

Product 1

HCID 68422745(3R,4S)-1-Benzyl-4-(4-benzyloxycarbonylamino-2-fluoro-phenyl)-pyrrolidine-3-carboxylic Acid Ethyl Ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4.5 g of 3-(4-benzyloxycarbonylamino-2-fluoro-phenyl)-acrylic acid ethyl ester (13.1 mmol) and 7.68 g N-[(pentyloxy)methyl]-N-[(trimethylsilyl)-methyl]-benzenemethanamine (26.2 mmol) in 50 ml dichloromethane was added 10 μL. trifluoroacetic acid. The reaction was monitored by TLC. The reaction was complete after 10 min. The mixture was diluted with dichloromethane, washed with sat. sodium bicarbonate solution and brine, dried over Mg sulfate, filtered and the filtrate evaporated. The residue was purified by filtration over a short silica column, using a 7/3 hexane/ethyl acetate mixture as eluent.

Workup

  1. washwashed with sat. sodium bicarbonate solution and brine
  2. dry with materialdried over Mg sulfate
  3. filtrationfiltered
  4. customthe filtrate evaporated
  5. filtrationThe residue was purified by filtration over a short silica column

Sources & evidence

ORD record
ord-1697577ddef14c7bb8aed7dfe81f25b5
Source dataset
uspto-grants-2012_12
Patent number
US08329908B2

Reaction notes

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