Trifluoroacetic acid → HCID 69939368, compound

HRID 1058242Notes

Reaction equation

HRID 1058242 reaction equation
C(O)(C(F)(F)F)=O.[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:31][N:32]2[CH2:35][C:34]([F:37])([F:36])[CH2:33]2)=[C:13]([CH:30]=1)[CH2:14][NH:15][C:16](=[O:29])[C@@H:17]1[CH2:21][CH2:20][CH2:19][N:18]1C(OC(C)(C)C)=O>C(Cl)Cl>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:31][N:32]2[CH2:33][C:34]([F:37])([F:36])[CH2:35]2)=[C:13]([CH:30]=1)[CH2:14][NH:15][C:16](=[O:29])[C@@H:17]1[CH2:21][CH2:20][CH2:19][NH:18]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 69939709HCID 69939709, compound

Product 1

HCID 69939368HCID 69939368, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (1 mL) was added to a stirred solution of N-{5-chloro-2-[(3,3-difluoroazetidin-1-yl)methyl]benzyl}-1-(tert-butoxycarbonyl)-L-prolinamide (64.2 mg, 0.14 mmol) in CH2Cl2 (2 ml) at 0° C. After 3 h, another 0.3 mL TFA was added. After 30 additional min the reaction mixture was concentrated and the residue was partitioned between CH2Cl2 and 10% NaHCO3. The CH2Cl2 layer was washed with water and brine, dried (Na2SO4) and evaporated to give N-{5-chloro-2-[(3,3-difluoroazetidin-1-yl)methyl]benzyl}-L-prolinamide (45.0 mg) as a glass: 1H NMR (CDCl3, 400 MHz) δ 1.70 (m, 2H), 1.90 (m, 2H), 2.16 (m, 1H), 2.85-3.04 (m, 2H), 3.58 (t, J=12.1 Hz, 4H), 3.73 (m, 3H), 4.37-4.52 (m, 2H), 7.19 (m, 2H), 7.32 (d, J=2.19 Hz, 1H), 8.45 (br s, 1H).

Workup

  1. concentrationAfter 30 additional min the reaction mixture was concentrated
  2. customthe residue was partitioned between CH2Cl2 and 10% NaHCO3
  3. washThe CH2Cl2 layer was washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-80242d574ccc400987068c4dcc56018c
Source dataset
uspto-grants-2003_02
Patent number
US06515011B2

Reaction notes

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