HCID 178453043, compound → HCID 178527617, compound

HRID 272228Notes

Reaction equation

HRID 272228 reaction equation
[F:1][C:2]([F:35])([F:34])[S:3]([O:6][C:7]1[CH:12]=[CH:11][C:10]([C@H:13]2[CH2:18][CH2:17][C@H:16]([N:19]([CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)C(OC(C)(C)C)=O)[CH2:15][CH2:14]2)=[CH:9][CH:8]=1)(=[O:5])=[O:4]>FC(F)(F)C(O)=O.ClCCl>[F:34][C:2]([F:1])([F:35])[S:3]([O:6][C:7]1[CH:8]=[CH:9][C:10]([C@H:13]2[CH2:18][CH2:17][C@H:16]([NH:19][CH2:27][C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH2:15][CH2:14]2)=[CH:11][CH:12]=1)(=[O:4])=[O:5]

Participants

4

Reactant 1

HCID 178453043HCID 178453043, compound

Product 1

HCID 178527617HCID 178527617, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 16.4 g of trans-4-{4-[benzyl(tert-butoxycarbonyl)amino]cyclohexyl}phenyl trifluoromethanesulfonate (32 mmol) in a mixture of trifluoroacetic acid (150 ml) and dichloromethane (900 ml) is stirred for 1 h 30. The solvents are evaporated under reduced pressure and then water, ethyl acetate and an aqueous ammonia solution are added. The organic phase is washed once with water and dried over sodium sulfate. trans-4-[4-(Benzylamino)cyclohexyl]-phenyl trifluoromethanesulfonate is obtained in the form of crystals (12.96 g, 98%) after evaporation of the solvents under reduced pressure. [M+H+]=414.2

Workup

  1. customThe solvents are evaporated under reduced pressure
  2. additionwater, ethyl acetate and an aqueous ammonia solution are added
  3. washThe organic phase is washed once with water
  4. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-82426d553f2943c5a580ea9a62fc25ee
Source dataset
uspto-grants-2008_11
Patent number
US07453010B2

Reaction notes

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