Trifluoroacetic acid → HCID 69040338, compound

HRID 1454248Notes

Reaction equation

HRID 1454248 reaction equation
C(OC(=O)[NH:7][C@@H:8]1[CH2:26][CH2:25][CH2:24][CH2:23][C@@:9]21[CH2:14][N:13]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)[CH2:12][CH2:11][CH2:10]2)(C)(C)C.FC(F)(F)C(O)=O.[OH-].[Na+]>ClCCl>[F:22][C:19]1[CH:18]=[CH:17][C:16]([CH2:15][N:13]2[CH2:12][CH2:11][CH2:10][C@@:9]3([CH2:23][CH2:24][CH2:25][CH2:26][C@H:8]3[NH2:7])[CH2:14]2)=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 69039795HCID 69039795, compound

Product 1

HCID 69040338HCID 69040338, compoundYield 1,085.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of [(6S,7R)-2-(4-fluorobenzyl)-2-aza-spiro[5.5]undec-7-yl]-carbamic acid tert-butyl ester (6.3 g, 1.4 mmol) in dichloromethane (30 mL) was treated with trifluoroacetic acid (30 mL) and stirred at room temperature for 1 hour. The solvent was removed under vacuum to give a residue. The residue was treated with 1.0 N aqueous sodium hydroxide. The mixture was extracted with dichloromethane and the organic phase was washed with water and saturated aqueous sodium chloride. The solvent was removed under vacuum to give an oil (4.2 g). 1H NMR (300 MHz, CDCl3) δ7.30-7.24 (m, 2H), 7.01-6.94 (m, 2H), 3.37 (m, 2H), 2.62 (m, 1H), 2.44 (m, 1H), 2.24 (m, 2H), 2.09 (m, 1H), 1.81 (m, 1H), 1.65-1.24 (m, 13H). Mass spec (ES+) m+/z 277.2 (M+H+).

Workup

  1. customThe solvent was removed under vacuum
  2. customto give a residue
  3. extractionThe mixture was extracted with dichloromethane
  4. washthe organic phase was washed with water and saturated aqueous sodium chloride
  5. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-2caede99f3cc4c56bf730d499caabce8
Source dataset
uspto-grants-2009_01
Patent number
US07479496B2

Reaction notes

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