Hydrochloric Acid → HCID 178468875, compound

HRID 272234Notes

Reaction equation

HRID 272234 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C@H:17]2[O:19][CH2:18]2)=[CH:11][C:10]=1[N:20](C(OC(C)(C)C)=O)[S:21]([CH3:24])(=[O:23])=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:32]([NH:39][C@H:40]1[CH2:45][CH2:44][C@H:43]([C:46]2[CH:56]=[CH:55][C:49]([C:50]([O:52][CH2:53][CH3:54])=[O:51])=[CH:48][CH:47]=2)[CH2:42][CH2:41]1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.Cl>C(O)C>[CH2:32]([N:39]([CH2:18][C@H:17]([OH:19])[CH2:16][O:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[C:10]([NH:20][S:21]([CH3:24])(=[O:22])=[O:23])[CH:11]=1)[C@H:40]1[CH2:41][CH2:42][C@H:43]([C:46]2[CH:47]=[CH:48][C:49]([C:50]([O:52][CH2:53][CH3:54])=[O:51])=[CH:55][CH:56]=2)[CH2:44][CH2:45]1)[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 112017484-benzyloxy-3-(N-tert-butoxycarbonyl-N-methylsulfonylamino)-1-((2S)-2,3-epoxypropoxy)benzeneHCID 178468874HCID 178468874, compound

Product 1

HCID 178468875HCID 178468875, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 818 mg (1.82 mmol) of 4-benzyloxy-3-(N-(tert-butoxycarbonyl)-N-(methylsulfonyl)amino)-1-((2S)-2,3-epoxypropoxy)benzene and of 450 mg (1.82 mmol) of ethyl trans-4-[4-(benzylamino)cyclohexyl]benzoate in the base form is heated at reflux in 15 ml of absolute ethanol for 16 h. The mixture is cooled, 3 ml of a saturated ethanolic hydrochloric acid solution are added thereto and the mixture is heated at 50° C. for 6 h. The solvent is evaporated and the residue is taken up with a mixture of 50 ml of a saturated sodium bicarbonate solution and 50 ml of ethyl acetate. The organic phase is washed with a saturated aqueous NaCl solution. The organic phase is dried and filtered, and the solvent is evaporated under reduced pressure. The crude product is purified by chromatography on a column of silica gel, elution being carried out with a methylene chloride/methanol/NH4OH (95/5/0.5) mixture. The title compound is obtained in the form of a white solid. [M+H+]=687.

Workup

  1. temperatureThe mixture is cooled
  2. customThe solvent is evaporated
  3. additionthe residue is taken up with a mixture of 50 ml of a saturated sodium bicarbonate solution and 50 ml of ethyl acetate
  4. washThe organic phase is washed with a saturated aqueous NaCl solution
  5. customThe organic phase is dried
  6. filtrationfiltered
  7. customthe solvent is evaporated under reduced pressure
  8. customThe crude product is purified by chromatography on a column of silica gel, elution

Sources & evidence

ORD record
ord-668bcdfc7ef0422aa9220bb6c9e0f320
Source dataset
uspto-grants-2008_11
Patent number
US07453010B2

Reaction notes

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