HCID 69359289, compound → HCID 69356572, compound

HRID 852651Notes

Reaction equation

HRID 852651 reaction equation
[CH2:1]([S:5]([N:8]([CH2:22][CH:23]=C)[C:9]1[CH:10]=[C:11]([CH:16]=[C:17]([CH2:19][CH2:20][CH3:21])[CH:18]=1)[C:12]([O:14][CH3:15])=[O:13])(=[O:7])=[O:6])[CH2:2][CH:3]=C>C(Cl)Cl.C1(P([Ru-2](Cl)(Cl)(P(C2CCCCC2)(C2CCCCC2)C2CCCCC2)=CC2C=CC=CC=2)(C2CCCCC2)C2CCCCC2)CCCCC1>[O:6]=[S:5]1(=[O:7])[CH2:1][CH2:2][CH:3]=[CH:23][CH2:22][N:8]1[C:9]1[CH:10]=[C:11]([CH:16]=[C:17]([CH2:19][CH2:20][CH3:21])[CH:18]=1)[C:12]([O:14][CH3:15])=[O:13]

Participants

4

Reactant 1

HCID 69359289HCID 69359289, compound

Product 1

HCID 69356572HCID 69356572, compoundYield 77.3%

Reagents, catalysts & solvents 2

HCID 178479816HCID 178479816, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 3-[(3-buten-1-ylsulfonyl)(2-propen-1-yl)amino]-5-propylbenzoate (D135) (1 g, 2.8 mmol, 1 equiv) in CH2Cl2 (200 ml) was added bis(tricyclohexylphosphino)benzylidene ruthenium (IV) dichloride (117 mg, 0.14 mmol, 0.05 equiv) and the resulting solution was stirred at room temperature for 48 h then concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (iso-hexane/AcOEt: 9:1) gave methyl 3-(1,1-dioxido-6,7-dihydro-1,2-thiazepin-2 (3H)-yl)-5-propylbenzoate (B117) (700 mg, 76%) as a pale purple oil. [M+H]+=324.4, RT=3.10 min.

Workup

  1. concentrationthen concentrated in vacuo
  2. customPurification of the residue by flash chromatography on silica gel (iso-hexane/AcOEt: 9:1)

Sources & evidence

ORD record
ord-374fae7bf86243b7bdc685fb0f5638ed
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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