Allyl bromide → HCID 131725705, compound

HRID 1796791Notes

Reaction equation

HRID 1796791 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([NH:18][CH:19]([C:25]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[O:26][SiH2:27][C:28]([CH3:31])([CH3:30])[CH3:29])[C:20]([OH:24])([CH3:23])[CH:21]=[CH2:22])(=[O:17])=[O:16])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:50](Br)[CH:51]=[CH2:52]>CN(C)C=O.C(OCC)(=O)C>[CH2:52]([N:18]([CH:19]([C:25]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)([C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)[O:26][SiH2:27][C:28]([CH3:31])([CH3:30])[CH3:29])[C:20]([OH:24])([CH3:23])[CH:21]=[CH2:22])[S:15]([C:12]1[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:14][CH:13]=1)(=[O:17])=[O:16])[CH:51]=[CH2:50]

Participants

6

Reactant 3

HCID 7841Allyl bromide2×HCID 10796Cesium carbonate2×HCID 131725706HCID 131725706, compound2×

Product 1

HCID 131725705HCID 131725705, compoundYield 102.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-benzyloxy-N-[1-(tert-butyl-diphenyl-silanyloxymethyl)-2-hydroxy-2-methyl-but-3-enyl]-benzenesulfonamide (compound of formula VI, 1.6 g, 2.6 mmol) in 5 ml of dimethylformamide was added cesium carbonate (1.7 g, 5.2 mmol) and allyl bromide (0.63 g, 5.2 mmol). After stirring at a temperature of about 20 to about 25° C. for about 24 hours, an additional 0.4 g of cesium carbonate and 0.2 ml of allyl bromide was added, and the mixture was stirred at a temperature of about 20° C. to about 25° C. for about 24 hours. The mixture was diluted with ethyl acetate, washed 4 times with water, dried over sodium sulfate, filtered and concentrated in vacuo to afford 1.75 g of N-allyl-4-benzyloxy-N-[1-(tert-butyl-diphenyl-silanyloxymethyl)-2-hydroxy-2-methyl-but-3-enyl]-benzenesulfonamide (compound of formula VII) as a colorless syrup.

Workup

  1. stirringthe mixture was stirred at a temperature of about 20° C. to about 25° C. for about 24 hours
  2. washwashed 4 times with water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-58816b47bc2d42a681a8d7cd53c8554c
Source dataset
uspto-grants-2006_04
Patent number
US07030242B2

Reaction notes

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