Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → methyl (2E)-3-(5-{2-[2-(acetylamino)-1,3-thiazol-4-yl]ethyl}-3-methylthiophen-2-yl)-2-propenoate

HRID 1892517Notes

Reaction equation

HRID 1892517 reaction equation
[CH:1]([C:3]1[S:7][C:6]([CH2:8][CH2:9][C:10]2[N:11]=[C:12]([NH:15][C:16](=[O:18])[CH3:17])[S:13][CH:14]=2)=[CH:5][C:4]=1[CH3:19])=O.C1(P(=[CH:39][C:40]([O:42][CH3:43])=[O:41])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)(Cl)Cl>[C:16]([NH:15][C:12]1[S:13][CH:14]=[C:10]([CH2:9][CH2:8][C:6]2[S:7][C:3](/[CH:1]=[CH:39]/[C:40]([O:42][CH3:43])=[O:41])=[C:4]([CH3:19])[CH:5]=2)[N:11]=1)(=[O:18])[CH3:17]

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 86650017N-{4-[2-(5-formyl-4-methylthiophen-2-yl)ethyl]-1,3-thiazol-2-yl}acetamide

Product 1

HCID 86650018methyl (2E)-3-(5-{2-[2-(acetylamino)-1,3-thiazol-4-yl]ethyl}-3-methylthiophen-2-yl)-2-propenoateYield 106.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of N-{4-[2-(5-formyl-4-methylthiophen-2-yl)ethyl]-1,3-thiazol-2-yl}acetamide (468.0 mg, 1.590 mmol) in chloroform (4.7 ml) was added dropwise a solution of methyl (triphenyl phosphoranylidene)acetate (797.4 mg, 2.385 mmol) in chloroform (2 ml) at 0° C. The mixture was allowed to warm to room temperature and stirred for 2 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (Merck 9385 60 g, ethyl acetate:dichloromethane=1:8) to give methyl (2E)-3-(5-{2-[2-(acetylamino)-1,3-thiazol-4-yl]ethyl}-3-methylthiophen-2-yl)-2-propenoate (591.6 mg, containing triphenylphosphineoxide) as a pale-yellow solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (Merck 9385 60 g, ethyl acetate:dichloromethane=1:8)

Sources & evidence

ORD record
ord-1a48f8b74d5844b3b3887dbf7ef37339
Source dataset
uspto-grants-2013_08
Patent number
US08507690B2

Reaction notes

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