Water → Methyl 3-[N-(p-chlorobenzyl)-5-allyloxy-3-(t-butylthio)indol-2-yl]-2,2-dimethylpropanoic acid

HRID 327232Notes

Reaction equation

HRID 327232 reaction equation
[Cl:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([OH:16])=[CH:13][CH:14]=3)[C:9]([S:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[C:8]2[CH2:22][C:23]([CH3:29])([CH3:28])[C:24]([O:26]C)=[O:25])=[CH:4][CH:3]=1.[C:32]([O-])([O-])=O.[K+].[K+].[CH2:38](Br)[CH:39]=[CH2:40].O>CN(C=O)C>[CH3:32][CH:22]([C:8]1[N:7]([CH2:6][C:5]2[CH:30]=[CH:31][C:2]([Cl:1])=[CH:3][CH:4]=2)[C:15]2[C:10]([C:9]=1[S:17][C:18]([CH3:21])([CH3:19])[CH3:20])=[CH:11][C:12]([O:16][CH2:38][CH:39]=[CH2:40])=[CH:13][CH:14]=2)[C:23]([CH3:29])([CH3:28])[C:24]([OH:26])=[O:25]

Participants

6

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 14980577Methyl 3-(3-(tert-butylthio)-1-(4-chlorobenzyl)-5-hydroxy-1H-indol-2-yl)-2,2-dimethylpropanoate

Product 1

HCID 19734346Methyl 3-[N-(p-chlorobenzyl)-5-allyloxy-3-(t-butylthio)indol-2-yl]-2,2-dimethylpropanoic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

500 mg. of methyl 3-[N-(p-chlorobenzyl)-5-hydroxy-3-(t-butylthio)indol-2-yl]-2,2-dimethylpropanoate from Step C of Example 1 was dissolved in 5 mL of DMF and 20 mg of K2CO3 and 150 mg of allyl bromide were added. The reaction was stirred for 16 hrs. Water was added and the organic phase extracted with EtOAc (3×5 mL). The organic phase was dried with MgSO4 and evaporated to yield, after chromatography on silica gel (EtOAc:hexane 1:5), the title compound.

Workup

  1. extractionthe organic phase extracted with EtOAc (3×5 mL)
  2. dry with materialThe organic phase was dried with MgSO4
  3. customevaporated
  4. customto yield

Sources & evidence

ORD record
ord-4c1ffa06c75c43bb9f9ed5faff454cda
Source dataset
uspto-grants-1993_12
Patent number
US05272145

Reaction notes

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