Hydrochloric Acid → HCID 58573329, compound

HRID 932283Notes

Reaction equation

HRID 932283 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]([CH2:25][CH:26]=[CH2:27])[C@:9]([NH:18][S@@](C(C)(C)C)=O)([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)[CH3:10])[CH:5]=[CH:6][CH:7]=1.Cl.C([O-])(O)=O.[Na+]>C1COCC1.O.CCOCC>[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]([CH2:25][CH:26]=[CH2:27])[C@@:9]([C:11]2[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=2)([NH2:18])[CH3:10])[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 58573987HCID 58573987, compound

Product 1

HCID 58573329HCID 58573329, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (R)—N-((2S,3R)-3-(3-chlorophenyl)-2-(4-chlorophenyl)hex-5-en-2-yl)-2-methylpropane-2-sulfinamide (Example 418, Step C, 5.96 g, 14.04 mmol) in THF (56.2 ml) was treated with. hydrochloric acid in water (36-38% wt, 6.40 ml, 211 mmol) for three hours. The reaction was diluted with 300 mL ether and the acidic aqueous layer made alkaline with sat. aq. NaHCO3 solution. The organic layer was washed with sat. aq. NaHCO3 solution, dried over MgSO4 and concentrated to provide the title compound as a colorless glass.

Workup

  1. washThe organic layer was washed with sat. aq. NaHCO3 solution
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-82f12f1ea408406cbf513c126a81b672
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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