Benzyl mercaptan → HCID 89444621, compound

HRID 1522772Notes

Reaction equation

HRID 1522772 reaction equation
[CH2:1]([SH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C1C=C(NC(N[C@@H]2CCCC[C@H]2N(C)C)=S)C=C(C(F)(F)F)C=1.[Cl:36][C:37]1[CH:38]=[C:39](/[C:44](/[C:62]([F:65])([F:64])[F:63])=[CH:45]\[C:46]([C:48]2[CH:60]=[CH:59][C:51]([C:52]([O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:53])=[C:50]([CH3:61])[CH:49]=2)=[O:47])[CH:40]=[C:41]([Cl:43])[CH:42]=1>C1(C)C=CC=CC=1>[CH2:1]([S:8][C:44]([C:39]1[CH:40]=[C:41]([Cl:43])[CH:42]=[C:37]([Cl:36])[CH:38]=1)([C:62]([F:63])([F:64])[F:65])[CH2:45][C:46]([C:48]1[CH:60]=[CH:59][C:51]([C:52]([O:54][C:55]([CH3:57])([CH3:58])[CH3:56])=[O:53])=[C:50]([CH3:61])[CH:49]=1)=[O:47])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7509Benzyl mercaptanHCID 114867661-[3,5-Bis(trifluoromethyl)phenyl]-3-[(1R,2R)-2-(dimethylamino)cyclohexyl]thioureaHCID 866959924-[(E)-3-(3,5-Dichloro-phenyl)-4,4,4-trifluoro-but-2-enoyl]-2-methyl-benzoic acid tert-butyl ester

Product 1

HCID 89444621HCID 89444621, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-40 °C

Procedure

Benzylmercaptan (1.5 eq.) and 1-[3,5-bis(trifluoromethyl)phenyl]-3-[(1R,2R)-2-(dimethylamino)cyclohexyl]thiourea (0.01 eq.) were added to a solution of tert-butyl 4-[(E)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-but-2-enoyl]-2-methyl-benzoate (200 mg) in toluene (1.5 mL) at −40° C. The solution was stirred at −40° C. for 6 hours then at room temperature for 17 hours. The reaction was quenched by the addition of a saturated solution of sodium chloride, and then extracted with ethylacetate. The collected organic phases were dried over magnesium sulfate, filtered and the filtrate was evaporated under vacuo. The residue was purified by chromatography on silica gel (eluent: cyclohexane/ethyl acetate) to give tert-butyl 4-[3-benzylsulfanyl-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-butanoyl]-2-methyl-benzoate (205 mg) as a mixture of two enantiomers.

Workup

  1. waitat room temperature for 17 hours
  2. customThe reaction was quenched by the addition of a saturated solution of sodium chloride
  3. extractionextracted with ethylacetate
  4. dry with materialThe collected organic phases were dried over magnesium sulfate
  5. filtrationfiltered
  6. customthe filtrate was evaporated under vacuo
  7. customThe residue was purified by chromatography on silica gel (eluent: cyclohexane/ethyl acetate)

Sources & evidence

ORD record
ord-0791cd0de37a40ebba7b2b226d149181
Source dataset
uspto-grants-2015_07
Patent number
US09078444B2

Reaction notes

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