Dichloromethane → (3S,4R)-4-(3-chlorophenyl)-3-(4-chlorophenyl)-3,4-dihydro-2H-1,2-thiazin

HRID 932038Notes

Reaction equation

HRID 932038 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]([CH:29]=[CH2:30])[C@H:9]([NH:17][S:18](/C=C/C2C=CC=CC=2)(=O)=O)[C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)[CH:5]=[CH:6][CH:7]=1.C(Cl)Cl>Cl[Ru](=CC1C=CC=CC=1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)Cl.ClCCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:8]2[CH:29]=[CH:30][S:18][NH:17][C@@H:9]2[C:10]2[CH:11]=[CH:12][C:13]([Cl:16])=[CH:14][CH:15]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 58573743(E)-N-((1S,2R)-2-(3-chlorophenyl)-1-(4-chlorophenyl)but-3-enyl)-2-phenylethenesulfonamide

Product 1

HCID 67999141(3S,4R)-4-(3-chlorophenyl)-3-(4-chlorophenyl)-3,4-dihydro-2H-1,2-thiazin

Reagents, catalysts & solvents 2

HCID 178479819HCID 178479819, compoundCatalystHCID 111,2-DichloroethaneSolvent

Conditions

Temperature
70 °C

Procedure

To a degassed solution of 7.29 g (15.90 mmol) of (E)-N-((1S,2R)-2-(3-chlorophenyl)-1-(4-chlorophenyl)but-3-enyl)-2-phenylethenesulfonamide (Example 117, Step A) in a 1:1 mixture of DCM (350 mL) and DCE (350 mL) was added Grubbs First Generation (1.20 g, 1.434 mmol). The resulting solution was stirred at 70° C. for 20 hours. After cooling to room temperature, the reaction was concentrated under reduced pressure. Purification by flash chromatography on silica gel (0 to 2% MeOH in DCM gradient) provided the title compound.

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe reaction was concentrated under reduced pressure
  3. customPurification by flash chromatography on silica gel (0 to 2% MeOH in DCM gradient)

Sources & evidence

ORD record
ord-5b8f2990e7294b03abd1e9453fa9f600
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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