Sodium Iodide → HCID 68541742, compound

HRID 1432112Notes

Reaction equation

HRID 1432112 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[CH:13]=[C:14]([CH:18]=[C:19]([O:21][CH3:22])[CH:20]=1)[C:15]([OH:17])=[O:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na+].[I-].[C:25]([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:32][CH2:33][CH:34]=[CH2:35]>CN(C=O)C.CC(OC)(C)C>[CH3:25][O:16][C:15](=[O:17])[C:14]1[CH:18]=[C:19]([O:21][CH3:22])[CH:20]=[C:12]([N:11]([C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:10])[CH2:32][CH2:33][CH:34]=[CH2:35])[CH:13]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 10796Cesium carbonateHCID 21241Homoallyl bromideHCID 68546183HCID 68546183, compound

Product 1

HCID 68541742HCID 68541742, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 0.75 g (2.38 mmol) 3-benzyloxycarbonylamino-5-methoxy-benzoic acid, 1.07 g (2.85 mmol) NaI, 2.3 g (7.14 mmol) Cs2CO3 and ca. 1 ml (10 mmol) 4-bromo-but-1-ene in 2 ml DMF is heated at 40° C. for 18 h. After cooling down the reaction mixture is diluted with TBME and washed with water. The organic phase is dried with sodium sulfate and evaporated. Purification of the crude product by chromatography on silica gel (hexane EtOAc 5:1) gives the 3-(benzyloxycarbonyl-but-3-enyl-amino)-5-methoxy-benzoic acid methyl ester.

Workup

  1. temperatureAfter cooling down the reaction mixture
  2. washwashed with water
  3. dry with materialThe organic phase is dried with sodium sulfate
  4. customevaporated
  5. customPurification of the crude product by chromatography on silica gel (hexane EtOAc 5:1)

Sources & evidence

ORD record
ord-ef44ecad0ce8435f9784915583d458b7
Source dataset
uspto-grants-2009_11
Patent number
US07612055B2

Reaction notes

Loading…