Hydrochloric Acid → HCID 56849004, compound

HRID 1473002Notes

Reaction equation

HRID 1473002 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][C:10]=1[CH:16]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:17][CH2:18][OH:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:33][S:34](Cl)(=[O:36])=[O:35].Cl>O>[CH3:33][S:34]([O:19][CH2:18][CH2:17][CH:16]([C:10]1[CH:11]=[C:12]([Br:15])[CH:13]=[CH:14][C:9]=1[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)(=[O:36])=[O:35]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 227351923-[2-(Benzyloxy)-5-bromophenyl]-3-phenylpropan-1-ol

Product 1

HCID 56849004HCID 56849004, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

500 ml MDC was added in the residue of 3-(2-(benzyloxy)-5-bromophenyl)-3-phenylpropan-1-ol of formula (C) followed by the addition of 50.1 g triethyl amine at 25° C. to 35° C. Reaction mass was cooled to 20° C. to 25° C. followed by the addition of 48.96 g methane sulphonyl chloride. Temperature was raised to 25° C. to 30° C. and maintained for 30 minutes. Further, 300 ml water was added and reaction mass was cooled to 0° C. to 5° C. and pH adjusted to 2 to 3 using 20% hydrochloric acid solution. The reaction temperature was raised to 25° C. to 35° C. and stirred for 30 minutes. The layers were separated and to the MDC layer added 5 g of activated charcoal and stirred for 30 minutes. MDC was distilled out under vacuum below 50° C. and co-distil by 2×50 ml methanol. The residue was treated with 300 ml methanol and heated up to 60° C. to 65° C. and maintained for 1 hour. Further, reaction mass was cooled to 25° C. to 35° C. and further cooled to 0° C. to 5° C. Finally the product was washed with 2×50 ml chilled methanol and dried in hot air oven at 55° C. to 60° C. to afford the title compound 3-(2-(benzyloxy)-5-bromophenyl)-3-phenylpropyl methanesulfonate of formula (D).

Workup

  1. customReaction mass
  2. temperaturewas cooled to 20° C. to 25° C.
  3. temperatureTemperature was raised to 25° C. to 30° C.
  4. temperaturemaintained for 30 minutes
  5. customreaction mass
  6. temperaturewas cooled to 0° C. to 5° C.
  7. temperatureThe reaction temperature was raised to 25° C. to 35° C.
  8. customThe layers were separated and to the MDC layer
  9. additionadded 5 g of activated charcoal
  10. stirringstirred for 30 minutes
  11. distillationMDC was distilled out under vacuum below 50° C. and co-distil by 2×50 ml methanol
  12. additionThe residue was treated with 300 ml methanol
  13. temperatureheated up to 60° C. to 65° C.
  14. temperaturemaintained for 1 hour
  15. customFurther, reaction mass
  16. temperaturewas cooled to 25° C. to 35° C.
  17. temperaturefurther cooled to 0° C. to 5° C
  18. washFinally the product was washed with 2×50 ml
  19. temperaturechilled methanol
  20. customdried in hot air oven at 55° C. to 60° C.

Sources & evidence

ORD record
ord-74140510f7dc41faa2bf6acf03e1640e
Source dataset
uspto-grants-2015_04
Patent number
US09012678B2

Reaction notes

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