Iodine → Anticancer agent 73

HRID 2263390Notes

Reaction equation

HRID 2263390 reaction equation
C(N(CC)CC)C.[CH2:8]([O:10][C:11](=[O:27])[CH:12]([NH:16][C:17](=[O:26])[C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1)[C:13](=O)[CH3:14])[CH3:9].II.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[CH2:8]([O:10][C:11]([C:12]1[N:16]=[C:17]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)[O:26][C:13]=1[CH3:14])=[O:27])[CH3:9]

Participants

6

Reactant 4

HCID 807IodineHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 15623096Ethyl 2-(4-methoxybenzamido)-3-oxobutanoate

Product 1

HCID 20064063Anticancer agent 73Yield 56.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

23.2 ml Triethylamine and a solution of 11.3 g 2-(4-methoxy-benzoylamino)-3-oxo-butyric acid ethyl ester in 200 ml dichloromethane were added sequentially to a stirred solution of 20.5 g iodine and 21.2 g triphenylphosphine in 500 ml dry dichloromethane. The reaction mixture was stirred at room temperature overnight. The solvent was evaporated in vacuo and the resulting residue purified by flash chromatography on silica gel to obtain 6.0 g 2-(4-methoxy-phenyl)-5-methyl-oxazole-4-carboxylic acid ethyl ester as pale yellow solid.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe resulting residue purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-219ab65ad6274850bc2341b13f838fe9
Source dataset
uspto-grants-2010_12
Patent number
US07851493B2

Reaction notes

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