Dichloromethane → HCID 178505060, compound

HRID 272230Notes

Reaction equation

HRID 272230 reaction equation
[F:1][C:2]([F:59])([F:58])[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]([CH2:51][C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)[CH2:20][C@H:21]([OH:50])[CH2:22][O:23][C:24]3[CH:29]=[CH:28][C:27]([O:30][CH2:31][C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)=[C:26]([N:38](C(OC(C)(C)C)=O)[S:39]([CH3:42])(=[O:41])=[O:40])[CH:25]=3)[CH2:15][CH2:14]2)=[CH:9][CH:8]=1)(=[O:5])=[O:4].ClCCl>FC(F)(F)C(O)=O>[F:58][C:2]([F:1])([F:59])[S:3]([O:6][C:7]1[CH:12]=[CH:11][C:10]([C@H:13]2[CH2:14][CH2:15][C@H:16]([N:19]([CH2:51][C:52]3[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=3)[CH2:20][C@H:21]([OH:50])[CH2:22][O:23][C:24]3[CH:29]=[CH:28][C:27]([O:30][CH2:31][C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)=[C:26]([NH:38][S:39]([CH3:42])(=[O:41])=[O:40])[CH:25]=3)[CH2:17][CH2:18]2)=[CH:9][CH:8]=1)(=[O:4])=[O:5]

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 178452895HCID 178452895, compound

Product 1

HCID 178505060HCID 178505060, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 1.4 g of trans-4-{4-[benzyl((2S)-3-{4-(benzyloxy)-3-[(tert-butoxycarbonyl)(methylsulfonyl)amino]phenoxy)-2-hydroxy-propyl)amino]cyclohexyl}phenyl trifluoromethanesulfonate (1.62 mmol) in a mixture of trifluoroacetic acid (5 ml) and of dichloromethane (45 mol) is stirred for 3 h 20. The solvents are evaporated under reduced pressure and then water, ethyl acetate and an aqueous ammonium solution are added. The organic phase is washed once with water and dried over sodium sulfate. trans-4-{4-[Benzyl((2S)-3-{4-(benzyloxy)-3-[(methylsulfonyl)amino]phenoxy}-2-hydroxypropyl)amino]cyclohexyl}phenyl trifluoromethanesulfonate is obtained in the form of an oil (1.27 g, 98%) after evaporation of the solvents under reduced pressure. [M+H+]=763.5.

Workup

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

Sources & evidence

ORD record
ord-2483d872736d4385a51064c23ef367b5
Source dataset
uspto-grants-2008_11
Patent number
US07453010B2

Reaction notes

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