Benzenesulfonyl chloride → 4-[2-(1-Benzenesulfonyl-piperidin-3-yloxy)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester

HRID 456463노트

반응식

HRID 456463 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH:21]2[CH2:26][CH2:25][CH2:24][N:23](C(OCC3C=CC=CC=3)=O)[CH2:22]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H].C(N(CC)CC)C.[C:46]1([S:52](Cl)(=[O:54])=[O:53])[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1>CO.[Pd].C(OCC)(=O)C.C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH:21]2[CH2:26][CH2:25][CH2:24][N:23]([S:52]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)(=[O:54])=[O:53])[CH2:22]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

9

반응물 4

HCID 7369Benzenesulfonyl chlorideHCID 8471Triethylamine2회HCID 694231604-[2-(1-Benzyloxycarbonyl-piperidin-3-yloxy)-phenyl]-piperazine-1-carboxylic acid tert-butyl esterHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 694221304-[2-(1-Benzenesulfonyl-piperidin-3-yloxy)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester수율 82%

시약·촉매·용매 4

HCID 23938Palladium촉매HCID 887Methanol용매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매2회

실험 절차

The compound of Step 1 (2.5 g, 4.7 mmol) was dissolved in methanol (20 mL). Palladium on carbon (50% water, 2.1 g) was added. A hydrogen atmosphere was established using balloons, and the mixture was stirred at r.t. for about 4 hours. The catalyst was removed by filtration with ethyl acetate through a bed of celite. The compound was isolated by running scrub-plug with a gradient of 100% ethyl acetate (200 mL) to triethylamine in ethyl acetate (10%). The isolated product (0.36 g, 0.9 mmol) was dissolved in methylene chloride (10 mL) at 0° C., and triethylamine (0.38 mL, 2.7 mmol) was added. Benzenesulfonyl chloride (0.15 mL, 1.1 mmol) was added drop wise to the reaction mixture. The solution warmed to r.t., concentrated under reduced pressure and purified using silica gel chromatography (75% ethyl acetate in hexanes) to afford the final compound (0.400 g, 82%).

후처리

  1. customThe catalyst was removed by filtration with ethyl acetate through a bed of celite
  2. customThe compound was isolated
  3. temperatureThe solution warmed to r.t.
  4. concentrationconcentrated under reduced pressure
  5. custompurified

출처 및 근거

ORD 기록
ord-c30e056c1f274e40a6386fd36084f046
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07186715B2

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