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

HRID 1590724노트

반응식

HRID 1590724 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-fb3e87bd314944a9a0db58cdef8088d5
출처 데이터셋
uspto-grants-1993_04
특허 번호
US05204344

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