Trifluoroacetic acid → HCID 69287216, compound

HRID 2225274Notes

Reaction equation

HRID 2225274 reaction equation
[OH:1][CH2:2][C@H:3]1[C@@H:8]([NH:9][C:10](=[O:25])[CH2:11][NH:12][C:13](=[O:24])[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)[CH2:7][CH2:6][C@@H:5]([N:26]([CH:34]([CH3:36])[CH3:35])C(=O)OC(C)(C)C)[CH2:4]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[OH:1][CH2:2][C@@H:3]1[CH2:4][C@H:5]([NH:26][CH:34]([CH3:36])[CH3:35])[CH2:6][CH2:7][C@@H:8]1[NH:9][C:10](=[O:25])[CH2:11][NH:12][C:13](=[O:24])[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69285460HCID 69285460, compound

Product 1

HCID 69287216HCID 69287216, compoundYield 95.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl(1R,3R,4S)-3-(hydroxymethyl)-4-(2-(3-(trifluoromethyl)-benzamido)acetamido)cyclohexyl(isopropyl)carbamate (130 mg) in CH2Cl2 is treated with CF3COOH (7 ml) and stirred at room temperature for 2 hours. The solution was evaporated and the residue neutralized with 1 N NaOH and extracted into CH2Cl2. The extract was washed with water, brine, dried over Na2SO4, filtered and the solvent evaporated to give 100 mg of the title compound as a white solid. 1H NMR (400 MHz, CDCl3) δ(TMS): 8.12 (s, 1 H), 8.03 (d, J=7.8 Hz, 1 H), 7.94 (bt, 1 H), 7.75 (d, J=7.8 Hz, 1 H), 7.57 (t, J=7.8 Hz,l H), 7.39 (bd, 1 H), 4.31 (m, 1 H), 4.26 (dd, J=5 Hz, J=16 Hz, 1 H), 4.13 (dd, J=5 Hz, J=16 Hz, 1 H), 3.42 (m, 1 H), 3.27 (m, 1 H), 3.05 (m, 1 H), 2.84 (m, 1 H), 1.92-1.60 (m, 8 H), 1.12 (d, J=6.3 Hz, 6 H). MS found: (M+H)+=416.38.

Workup

  1. customThe solution was evaporated
  2. extractionextracted into CH2Cl2
  3. washThe extract was washed with water, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent evaporated

Sources & evidence

ORD record
ord-3ede60d8ba0f47af8564af51978d4b78
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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