Ethanol → HCID 86583575, compound

HRID 1841770Notes

Reaction equation

HRID 1841770 reaction equation
C([O:8][CH2:9][CH2:10][O:11][C:12]1[C:17]([I:18])=[CH:16][C:15]([CH2:19][CH3:20])=[CH:14][C:13]=1[CH:21]([NH:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]#[N:35])=[CH:30][CH:29]=1)[C:22]([O:24][CH2:25][CH3:26])=[O:23])C1C=CC=CC=1.I[Si](C)(C)C.C(O)C>ClCCl>[C:34]([C:31]1[CH:32]=[CH:33][C:28]([NH:27][CH:21]([C:13]2[CH:14]=[C:15]([CH2:19][CH3:20])[CH:16]=[C:17]([I:18])[C:12]=2[O:11][CH2:10][CH2:9][OH:8])[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:29][CH:30]=1)#[N:35]

Participants

5

Reactant 3

HCID 702EthanolHCID 85247Trimethylsilyl iodide2×HCID 86583576HCID 86583576, compound

Product 1

HCID 86583575HCID 86583575, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 7.1 g of ethyl (RS)-[2-(2-benzyloxy-ethoxy)-5-ethyl-3-iodo-phenyl]-(4-cyano-phenylamino)-acetate in 50 ml of dichloromethane was treated with 7.29 g of iodotrimethylsilane. After 12 hours at room temperature the same amount of iodo-trimethylsilane was added and the mixture was stirred for 18 hours at room temperature. Then, ethanol was added. The reaction mixture was concentrated, poured on to ice/aqueous sodium bisulphite solution and extracted with ethyl acetate. The organic phases were washed with aqueous sodium hydrogen carbonate solution and ice-water, dried over sodium sulphate and concentrated. Crystallization of the residue gave 3.8 g of ethyl (RS)-(4-cyano-phenylamino)-[5-ethyl-2-(2-hydroxy-ethoxy)-3-iodo-phenyl]-acetate. Chromatography of the mother liquor on silica gel gave an additional 1.83 g of product; MS (ISP) m/z 495 (M+H)+, 517 (M+Na)+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionpoured on to ice/aqueous sodium bisulphite solution
  3. extractionextracted with ethyl acetate
  4. washThe organic phases were washed with aqueous sodium hydrogen carbonate solution and ice-water
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated
  7. customCrystallization of the residue

Sources & evidence

ORD record
ord-0c49e24e13344e62b52898d40a6cb8e1
Source dataset
uspto-grants-2004_01
Patent number
US06683215B2

Reaction notes

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