Trifluoroacetic acid → HCID 9995796, compound

HRID 1714928Notes

Reaction equation

HRID 1714928 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:30]=[CH:29][C:18]3[CH2:19][CH2:20][N:21]([CH:24]4[CH2:28][CH2:27][CH2:26][CH2:25]4)[CH2:22][CH2:23][C:17]=3[CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH:24]1([N:21]2[CH2:22][CH2:23][C:17]3[CH:16]=[C:15]([O:14][CH:11]4[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]4)[CH:30]=[CH:29][C:18]=3[CH2:19][CH2:20]2)[CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 10341753HCID 10341753, compound

Product 1

HCID 9995796HCID 9995796, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(3-Cyclopentyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yloxy)-piperidine-1-carboxylic acid-tert-butyl ester (E5a) (593 mg, 1.43 mmol) was dissolved in dichloromethane (5 ml) and treated with trifluoroacetic acid (3 ml). The solution was stirred at room temperature for 1 hour, concentrated in vacuo and applied to a SCX ion exchange cartridge (Varian bond-elute, 5 g) and washed with methanol and then a mixture of 0.880 ammonia:methanol (1:9). The combined basic fractions were concentrated in vacuo and the resulting residue was purified by column chromatography eluting with a mixture of 0.880 ammonia:methanol:dichloromethane (1:9:90) to afford the title product (E5). MS (ES+) m/e 315 [M+H]+.

Workup

  1. concentrationconcentrated in vacuo
  2. washwashed with methanol
  3. additiona mixture of 0.880 ammonia:methanol (1:9)
  4. concentrationThe combined basic fractions were concentrated in vacuo
  5. customthe resulting residue was purified by column chromatography
  6. washeluting with a mixture of 0.880 ammonia:methanol:dichloromethane (1:9:90)

Sources & evidence

ORD record
ord-a503db7017d74550a2cc086a7628fca5
Source dataset
uspto-grants-2010_09
Patent number
US07799773B2

Reaction notes

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