Ethanol → HCID 86583575, compound

HRID 1016806Notes

Reaction equation

HRID 1016806 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 iodotrimethylsilane 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-295e8baac6d849a0a38d6c3faf1cc1e5
Source dataset
uspto-grants-2002_11
Patent number
US06476264B2

Reaction notes

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