Trifluoroacetic acid → HCID 70171489, compound

HRID 2306267Notes

Reaction equation

HRID 2306267 reaction equation
[CH:1]([Si:4]([O:11][C:12](=[O:43])[N:13]([C@H:31]1[CH2:35][CH2:34][N:33](C(OC(C)(C)C)=O)[CH2:32]1)[CH2:14][CH2:15][C:16]1[N:20]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]#[N:29])=[C:24]([F:30])[CH:23]=2)[CH:19]=[N:18][CH:17]=1)([CH:8]([CH3:10])[CH3:9])[CH:5]([CH3:7])[CH3:6])([CH3:3])[CH3:2].C(O)(C(F)(F)F)=O.C(N(CC)CC)C>C(Cl)Cl.O>[CH:1]([Si:4]([O:11][C:12](=[O:43])[N:13]([CH2:14][CH2:15][C:16]1[N:20]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]#[N:29])=[C:24]([F:30])[CH:23]=2)[CH:19]=[N:18][CH:17]=1)[C@H:31]1[CH2:35][CH2:34][NH:33][CH2:32]1)([CH:5]([CH3:6])[CH3:7])[CH:8]([CH3:9])[CH3:10])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 70169699HCID 70169699, compound

Product 1

HCID 70171489HCID 70171489, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

(S)-N-[1-(tert-Butoxycarbonyl)pyrrolidin-3-yl]-N-{2-[1-(4-cyano-3-fluorobenzyl)-1H-imidazol-5-yl]ethyl}carbamic acid triisopropylsilyl ester, as described above in Step G, (395 mg, 0.643 mmol) was dissolved in CH2Cl2 (10 mL) and TFA (2 mL, 2.56 mmol) was added. After 2 hours, the reaction was neutralized with triethylamine, diluted with water and extracted with CH2Cl2 (3×). The combined organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo, to yield the above-titled compound.

Workup

  1. extractionextracted with CH2Cl2 (3×)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b9fef852e89342179608185b8e6aadd5
Source dataset
uspto-grants-2002_08
Patent number
US06441017B1

Reaction notes

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