Hydrochloric Acid → N-[2-Benzyloxy-5-({(2S)-2-hydroxy-3-[(1,2,3,4-tetrahydro-2-naphthalenylmethyl)amino]propyl}oxy)-phenyl]methanesulfonamide

HRID 1242850Notes

Reaction equation

HRID 1242850 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]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH2:35][CH2:34][CH:33]1[CH2:42][NH2:43].Cl>C(O)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C@@H:17]([OH:19])[CH2:18][NH:43][CH2:42][CH:33]2[CH2:34][CH2:35][C:36]3[C:41](=[CH:40][CH:39]=[CH:38][CH:37]=3)[CH2:32]2)=[CH:11][C:10]=1[NH:20][S:21]([CH3:24])(=[O:22])=[O:23])[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 157186321,2,3,4-Tetrahydronaphthalen-2-ylmethanamine

Product 1

HCID 12071250N-[2-Benzyloxy-5-({(2S)-2-hydroxy-3-[(1,2,3,4-tetrahydro-2-naphthalenylmethyl)amino]propyl}oxy)-phenyl]methanesulfonamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
50 °C

Procedure

A mixture of 770 mg of 4-benzyloxy-3-(N-tert-butoxycarbonyl-N-methylsulfonylamino)-1-((2S)2,3-epoxypropoxy)benzene (1.71 mmol) and 300 mg (1.8 mmol) of 1,2,3,4-tetrahydronaphthalen-2-ylmethylamine, obtained as described in EP-A-436435, in 20 ml of absolute ethanol is heated under reflux for 16 hours. The mixture is cooled, 3 ml of an ethanol solution saturated with hydrochloric acid are added thereto and the medium is heated at 50° C. for 5 hours. The solvent is evaporated and the medium 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, filtered and the solvent is evaporated under reduced pressure. The crude product is purified by chromatography on a silica gel column, eluting with a methylene chloride/methanol=95/5 mixture. The title compound is obtained in the form of a glassy solid.

Workup

  1. customobtained
  2. temperatureis heated
  3. temperatureunder reflux for 16 hours
  4. temperatureThe mixture is cooled
  5. customThe solvent is evaporated
  6. additionthe medium is taken up with a mixture of 50 ml of a saturated sodium bicarbonate solution and 50 ml of ethyl acetate
  7. washThe organic phase is washed with a saturated aqueous NaCl solution
  8. customThe organic phase is dried
  9. filtrationfiltered
  10. customthe solvent is evaporated under reduced pressure
  11. customThe crude product is purified by chromatography on a silica gel column
  12. washeluting with a methylene chloride/methanol=95/5 mixture

Sources & evidence

ORD record
ord-625caa9155ac44b5af06dc91d9b448e8
Source dataset
uspto-grants-2006_10
Patent number
US07115780B2

Reaction notes

Loading…