Trifluoroacetic acid → HCID 178511301, compound

HRID 1159364Notes

Reaction equation

HRID 1159364 reaction equation
FC(F)(F)C(O)=O.[N:8]1([CH2:13][C:14]2[CH:33]=[CH:32][C:17]([O:18][C@H:19]3[CH2:22][C@H:21]([CH2:23][NH:24]C(=O)OC(C)(C)C)[CH2:20]3)=[CH:16][CH:15]=2)[CH2:12][CH2:11][CH2:10][CH2:9]1>ClCCl>[N:8]1([CH2:13][C:14]2[CH:33]=[CH:32][C:17]([O:18][C@H:19]3[CH2:22][C@H:21]([CH2:23][NH2:24])[CH2:20]3)=[CH:16][CH:15]=2)[CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178453658HCID 178453658, compound2×

Product 1

HCID 178511301HCID 178511301, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoro-acetic acid (3.5 mL, 49 mmol) was added to a solution of Example 38, tert-butyl ({trans-3-[4-(pyrrolidin-1-ylmethyl)phenoxy]cyclobutyl}methyl)carbamate (2.16 g, 6 mmol) in dichloro-methane (20 mL). The reaction mass was stirred at room temperature for 2 h and evaporated in vacuo. The residue was diluted with water (50 mL), and the obtained solution was extracted with CH2Cl2. The organic layer was discarded. The aqueous one was alkalized with 10 N NaOH to pH 12 and extracted with CHCl3 (3×50 mL). The combined extracts were dried and evaporated to afford the title compound (1.4 g, 91%) as a yellow oil. LCMS-data: M+H 261.2, 262.2 (calc 260.38). 1H NMR-data (DMSO-d6): 7.17 (d, 2H, Ph, J=8.6 Hz); 6.72 (d, 2H, Ph, J=8.6 Hz); 4.65-4.76 (m, 1H); 3.47 (s, 3H, CH2); 2.63 (d, 2H, CH2, J=6.6 Hz); 2.32-2.42 (m, 4H); 2.18-2.28 (m, 3H); 2.00-2.13 (m, 2H); 1.60-1.72 (m, 4H).

Workup

  1. customevaporated in vacuo
  2. additionThe residue was diluted with water (50 mL)
  3. extractionthe obtained solution was extracted with CH2Cl2
  4. extractionextracted with CHCl3 (3×50 mL)
  5. customThe combined extracts were dried
  6. customevaporated

Sources & evidence

ORD record
ord-eb150da7bfd34af69da7c11e6edef792
Source dataset
uspto-grants-2010_10
Patent number
US07812040B2

Reaction notes

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