Trifluoroacetic acid → HCID 22082733, compound

HRID 2187424Notes

Reaction equation

HRID 2187424 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[CH:16][CH:17]=[C:18]3[C:23]=2[CH2:22][C@H:21]([NH:24][C:25]([C:27]2[CH:32]=[CH:31][C:30]([N:33]4[CH2:38][CH2:37][O:36][CH2:35][CH2:34]4)=[CH:29][CH:28]=2)=[O:26])[CH2:20][CH2:19]3)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[N:11]1([C:14]2[CH:15]=[CH:16][CH:17]=[C:18]3[C:23]=2[CH2:22][C@H:21]([NH:24][C:25](=[O:26])[C:27]2[CH:32]=[CH:31][C:30]([N:33]4[CH2:34][CH2:35][O:36][CH2:37][CH2:38]4)=[CH:29][CH:28]=2)[CH2:20][CH2:19]3)[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22082763HCID 22082763, compound

Product 1

HCID 22082733HCID 22082733, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice-cooled solution of (R)-N-[8-(4-tert-butyloxycarbonylpiperazin-1-yl)-1,2,3,4-tetrahydro-2-naphthyl]-4-morpholinophenylcarboxamide (1.0 g, 2 mmol) in methylene chloride (100 mL) was added trifluoroacetic acid (3 mL). The reaction was stirred at ambient temperature for 7 h. The solvent was evaporated in vacuo and the residue was dissolved in water (20 mL), alkalized with a 2 M aqueous sodium hydroxide solution and extracted, twice, with methylene chloride. The phases were separated, the combined organic phases were dried (Na2SO4), filtered and evaporated in vacuo. Purification on a silica gel column using chloroform/methanol/concentrated ammonium hydroxide (95:5:0.5) as the eluent gave 580 mg (70% yield) of the title compound as white crystals: mp 202-203° C.; [α]21D −56° (c 1.0, chloroform); EIMS (70 eV) m/z (relative intensity) 420 (5, M+).

Workup

  1. customThe solvent was evaporated in vacuo
  2. dissolutionthe residue was dissolved in water (20 mL)
  3. extractionextracted
  4. customThe phases were separated
  5. dry with materialthe combined organic phases were dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customPurification on a silica gel column

Sources & evidence

ORD record
ord-aa03fe5c44a44d6299c16d38c0eb4d13
Source dataset
uspto-grants-2002_06
Patent number
US06410530B1

Reaction notes

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