4-benzyloxy-3-(N-tert-butoxycarbonyl-N-methylsulfonylamino)-1-((2S)-2,3-epoxypropoxy)benzene → HCID 178452895, compound

HRID 272229Notes

Reaction equation

HRID 272229 reaction equation
[F:1][C:2]([F:28])([F:27])[S:3]([O:6][C:7]1[CH:12]=[CH:11][C:10]([C@H:13]2[CH2:18][CH2:17][C@H:16]([NH:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:15][CH2:14]2)=[CH:9][CH:8]=1)(=[O:5])=[O:4].[CH2:29]([O:36][C:37]1[CH:42]=[CH:41][C:40]([O:43][CH2:44][C@H:45]2[O:47][CH2:46]2)=[CH:39][C:38]=1[N:48]([C:53]([O:55][C:56]([CH3:59])([CH3:58])[CH3:57])=[O:54])[S:49]([CH3:52])(=[O:51])=[O:50])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C(O)C>[F:28][C:2]([F:27])([F:1])[S:3]([O:6][C:7]1[CH:8]=[CH:9][C:10]([C@H:13]2[CH2:18][CH2:17][C@H:16]([N:19]([CH2:20][C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH2:46][C@H:45]([OH:47])[CH2:44][O:43][C:40]3[CH:41]=[CH:42][C:37]([O:36][CH2:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[C:38]([N:48]([C:53]([O:55][C:56]([CH3:59])([CH3:58])[CH3:57])=[O:54])[S:49]([CH3:52])(=[O:50])=[O:51])[CH:39]=3)[CH2:15][CH2:14]2)=[CH:11][CH:12]=1)(=[O:4])=[O:5]

Participants

4

Reactant 2

HCID 112017484-benzyloxy-3-(N-tert-butoxycarbonyl-N-methylsulfonylamino)-1-((2S)-2,3-epoxypropoxy)benzeneHCID 178527617HCID 178527617, compound

Product 1

HCID 178452895HCID 178452895, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5.52 g of trans-4-[4-(benzylamino)cyclohexyl]phenyl trifluoromethanesulfonate (13.3 mmol) and of 5 g of 4-benzyloxy-3-(N-(tert-butoxycarbonyl)-N-(methylsulfonyl)amino)-1-((2S)-2,3-epoxypropoxy)benzene (11.2 mmol) in ethanol (72 ml) is brought to reflux for 5 h. The solvent is evaporated under reduced pressure and trans-4-{4-[benzyl((2S)-3-{4-(benzyloxy)-3-[(tert-butoxycarbonyl)(methylsulfonyl)amino]phenoxy}-2-hydroxypropyl)amino]cyclohexyl}phenyl trifluoromethanesulfonate is obtained in the form of an oil (6.94 g, 72%) after purification on silica gel (eluent: dichloromethane/methanol 98/2). [M+H+]=863.4

Workup

  1. temperatureto reflux for 5 h
  2. customThe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-4f2da2c08a6b45c5b6d3e802e47d7a3a
Source dataset
uspto-grants-2008_11
Patent number
US07453010B2

Reaction notes

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