Hydrochloric Acid → HCID 178472988, compound

HRID 272233Notes

Reaction equation

HRID 272233 reaction equation
[CH2:1]([NH:8][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.[CH2:28]([O:35][C:36]1[CH:41]=[CH:40][C:39]([O:42][CH2:43][C@H:44]2[O:46][CH2:45]2)=[CH:38][C:37]=1[N:47](C(OC(C)(C)C)=O)[S:48]([CH3:51])(=[O:50])=[O:49])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.Cl>C(O)C>[CH2:1]([N:8]([CH2:45][C@H:44]([OH:46])[CH2:43][O:42][C:39]1[CH:40]=[CH:41][C:36]([O:35][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[C:37]([NH:47][S:48]([CH3:51])(=[O:50])=[O:49])[CH:38]=1)[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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 112017484-benzyloxy-3-(N-tert-butoxycarbonyl-N-methylsulfonylamino)-1-((2S)-2,3-epoxypropoxy)benzeneHCID 178472987HCID 178472987, compound

Product 1

HCID 178472988HCID 178472988, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
50 °C

Procedure

A mixture of 3.22 g of ethyl trans-{4-[4-(benzylamino)cyclohexyl]phenoxy}acetate (8.7 mmol) and 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 40 h. A 3N solution of hydrochloric acid in ethanol is added and the reaction medium is heated at 50° C. for 19 h. The solvents are evaporated under reduced pressure and then water, dichloromethane and a saturated aqueous sodium carbonate solution are added. The aqueous phase is extracted once with dichloromethane. The organic phases are combined, washed with water and then dried over magnesium sulfate. The solvents are evaporated under reduced pressure and ethyl trans-(4-{4-[Benzyl((2S)-3-{4-(benzyloxy)-3-[(methylsulfonyl)amino]phenoxy}-2-hydroxypropyl)amino]cyclohexyl}phenoxy)acetate is obtained in the form of an oil (2.7 g, 43%) after purification on silica gel (eluent: ethyl acetate/heptane 30/70 to 50/50 gradient in 40 min). [M+H+]=717.6

Workup

  1. temperatureto reflux for 40 h
  2. customThe solvents are evaporated under reduced pressure
  3. additionwater, dichloromethane and a saturated aqueous sodium carbonate solution are added
  4. extractionThe aqueous phase is extracted once with dichloromethane
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. customThe solvents are evaporated under reduced pressure

Sources & evidence

ORD record
ord-01cbd8f1621547f4aba4cd0a2950084d
Source dataset
uspto-grants-2008_11
Patent number
US07453010B2

Reaction notes

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