Hydrochloric Acid → HCID 66781214, compound

HRID 1096759Notes

Reaction equation

HRID 1096759 reaction equation
C1(S([C:10]2(SC)[CH2:15][C@@H:14]3[C@@:12]([C:16]4[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=4)([CH2:13]3)[CH2:11]2)(=O)=O)C=CC=CC=1.C[OH:27].Cl>C(OCC)(=O)C.CCCCCC>[Cl:23][C:18]1[CH:17]=[C:16]([C@@:12]23[CH2:13][C@@H:14]2[CH2:15][C:10](=[O:27])[CH2:11]3)[CH:21]=[CH:20][C:19]=1[Cl:22]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 86622519HCID 86622519, compound

Product 1

HCID 66781214HCID 66781214, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

(1R,5R)-3-Benzenesulfonyl-1-(3,4-dichlorophenyl)-3-methylsulfanyl-bicyclo[3.1.0]hexane (1.4 g, 3.3 mmol), methanol (6 mL) and concentrated hydrochloric acid (1.5 mL) were heated to reflux for 7 hours. The reaction was monitored by TLC (ethyl acetate/hexane (20:80)). The reaction mixture was concentrated under reduced pressure to remove methanol. The pH of the reaction mass was adjusted to 8-9 with saturated sodium bicarbonate solution. The aqueous layer was extracted with diethyl ether (100 mL). The organic layer was washed with water, dried over anhydrous sodium sulphate, filtered and evaporated under reduced pressure to yield 1.1 g of crude oil, which was purified by preparative HPLC to yield 560 mg (70%) of 99% pure product. 1H NMR δ(300 MHz,CDCl3) 0.67-0.70 (1H,t, J=4 Hz), 1.25-1.35 (1H,m), 1.94-2.15 (1H,m), 2.36-2.42 (1H,d ,J=18 Hz), 2.59-2.65 (1H,d,J=18 Hz), 2.83-2.89 (2H,m),6.99-7.03 (1H,dd,J=9.3 Hz), 7.25-7.26 (1H,d,J=3 Hz),7.36-7.39 (1H,d,J=9 Hz). 13CNMR(CDCl3) δ: 215.25, 143.49, 132.55, 130.39, 130.06, 128.07, 125.40, 45.34, 42.08, 27.18, 23.32, 22.24.

Workup

  1. temperatureto reflux for 7 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customto remove methanol
  4. extractionThe aqueous layer was extracted with diethyl ether (100 mL)
  5. washThe organic layer was washed with water
  6. dry with materialdried over anhydrous sodium sulphate
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customto yield 1.1 g of crude oil, which
  10. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-434bdcc53f804bebbb0b5d943a409c7d
Source dataset
uspto-grants-2012_03
Patent number
US08138377B2

Reaction notes

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