Methyl iodide → 5(S)-[1(S)-(Boc-Amino)-2-(p-methoxyphenyl)ethyl]dihydrofuran-2-(3H)-one

HRID 1585319Notes

Reaction equation

HRID 1585319 reaction equation
[C:1]([NH:8][C@H:9]([C@H:18]1[O:22][C:21](=[O:23])[CH2:20][CH2:19]1)[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:24]([O-])([O-])=O.[Cs+].[Cs+].CI>CN(C=O)C.O1CCOCC1>[C:1]([NH:8][C@H:9]([C@H:18]1[O:22][C:21](=[O:23])[CH2:20][CH2:19]1)[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:24])=[CH:13][CH:12]=1)([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 539985235(S)-[1(S)-(Boc-amino)-2-(p-hydroxyphenyl)ethyl]dihydrofuran-2-(3H)-one

Product 1

HCID 537063315(S)-[1(S)-(Boc-Amino)-2-(p-methoxyphenyl)ethyl]dihydrofuran-2-(3H)-one

Reagents, catalysts & solvents 1

HCID 217120691,4-dioxane N,N-dimethylformamideSolvent

Procedure

A suspension of 4.00 g (12.44 mmol) of 5(S)-[1(S)-(Boc-amino)-2-(p-hydroxyphenyl)-ethyl]dihydrofuran-2-(3H)-one (Example 11f)) in 240 ml of DMF/dioxane, 1:1, is reacted, under an N2 atmosphere, with 8.1 g (24.88 mmol) of Cs2CO3 and 0.77 ml (12.44 mmol) of methyl iodide. After 18 h, the reaction mixture is poured onto 190 ml of ice-water, and this mixture is extracted 3× with methylene chloride. The organic phases are washed with water and saline, dried with Na2SO4 and evaporated. Stirring with hexane in an ultrasonication bath affords the title compound: TLC Rf (C)=0.43; tRet (II)=13.5 min; FAB-MS (M+H)+ =336.

Workup

  1. extractionthis mixture is extracted 3× with methylene chloride
  2. washThe organic phases are washed with water and saline
  3. dry with materialdried with Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-a2dce09ef35e4e7f8b3844ff01a2a7bb
Source dataset
uspto-grants-1999_08
Patent number
US05935976

Reaction notes

Loading…