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

HRID 1590724ノート

反応式

HRID 1590724 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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 (3×5mL). The organic phase was dried with MgSO4 and evaporated to yield, after chromatography on silica gel (EtOAc:hexane 1:5), the title compound.

後処理

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

出典と根拠

ORDレコード
ord-fb3e87bd314944a9a0db58cdef8088d5
出典データセット
uspto-grants-1993_04
特許番号
US05204344

反応ノート

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