HCID 178472989, compound → HCID 178472987, compound

HRID 272232Notes

Reaction equation

HRID 272232 reaction equation
[CH2:1]([N:8](C(OC(C)(C)C)=O)[C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]2[CH:27]=[CH:26][C:18]([O:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:17][CH:16]=2)[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>FC(F)(F)C(O)=O.ClCCl>[CH2:1]([NH:8][C@H:9]1[CH2:10][CH2:11][C@H:12]([C:15]2[CH:27]=[CH:26][C:18]([O:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:17][CH:16]=2)[CH2:13][CH2:14]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 178472989HCID 178472989, compound

Product 1

HCID 178472987HCID 178472987, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 4.5 g of ethyl trans-(4-{4-[benzyl(tert-butoxycarbonyl)amino]cyclohexyl}-phenoxy)acetate (9.6 mmol) in a mixture of trifluoroacetic acid (30 ml) and dichloromethane (90 ml) is stirred for 2 h. The solvents are evaporated under reduced pressure and then water, ethyl acetate and a saturated aqueous sodium carbonate solution are added. The organic phase is washed once with water and dried over sodium sulfate. Ethyl trans-{4-[4-(benzylamino)cyclohexyl]phenoxy}acetate is obtained in the form of an oil (3.22 g, 88%) after evaporation of the solvents under reduced pressure. [M+H+]=368.3

Workup

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

Sources & evidence

ORD record
ord-112b3ad74b5c46e29f955f918bf79ebf
Source dataset
uspto-grants-2008_11
Patent number
US07453010B2

Reaction notes

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