4-(Methanesulfonyl)benzoyl chloride → 4-({Ethyl-[7-(4-methanesulfonyl-benzoylamino)-1,2,3,4-tetrahydro-naphthalen-2-yl]-amino}-methyl)-piperidine-1-carboxylic acid tert-butyl ester

HRID 983457

반응식

HRID 983457 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][N:15]([CH:18]2[CH2:27][CH2:26][C:25]3[C:20](=[CH:21][C:22]([NH2:28])=[CH:23][CH:24]=3)[CH2:19]2)[CH2:16][CH3:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:29][S:30]([C:33]1[CH:41]=[CH:40][C:36]([C:37](Cl)=[O:38])=[CH:35][CH:34]=1)(=[O:32])=[O:31]>CCOC(C)=O.C(=O)([O-])[O-].[K+].[K+]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][N:15]([CH2:16][CH3:17])[CH:18]2[CH2:27][CH2:26][C:25]3[C:20](=[CH:21][C:22]([NH:28][C:37](=[O:38])[C:36]4[CH:35]=[CH:34][C:33]([S:30]([CH3:29])(=[O:32])=[O:31])=[CH:41][CH:40]=4)=[CH:23][CH:24]=3)[CH2:19]2)[CH2:10][CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

참가 물질

5

반응물 2

HCID 112760134-(Methanesulfonyl)benzoyl chlorideHCID 686243034-{[(7-Amino-1,2,3,4-tetrahydro-naphthalen-2-yl)-ethyl-amino]-methyl}-piperidine-1-carboxylic acid tert-butyl ester

생성물 1

HCID 686234154-({Ethyl-[7-(4-methanesulfonyl-benzoylamino)-1,2,3,4-tetrahydro-naphthalen-2-yl]-amino}-methyl)-piperidine-1-carboxylic acid tert-butyl ester수율 60.3%

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매2회HCID 11430Potassium Carbonate용매

실험 절차

To a solution of 4-{[(7-amino-1,2,3,4-tetrahydro-naphthalen-2-yl)-ethyl-amino]-methyl}-piperidine-1-carboxylic acid tert-butyl ester (1.5 g, 3.87 mmol) in EtOAc (50 mL) and 20% aq. potassium carbonate (50 mL) was added 4-methanesulfonyl-benzoyl chloride (760 mg, 4.1 mmol) dropwise in EtOAc (75 mL). The reaction was stirred at room temperature overnight and the layers separated. The EtOAc layer was concentrated onto silica gel and placed on top of a flash column. The column was eluted with 35% acetone in hexanes. Product containing fractions were pooled and concentrated to afford 4-({ethyl-[7-(4-methanesulfonyl-benzoylamino)-1,2,3,4-tetrahydro-naphthalen-2-yl]-amino}-methyl)-piperidine-1-carboxylic acid tert-butyl ester as a light pink solid (1.33 g).

후처리

  1. customthe layers separated
  2. concentrationThe EtOAc layer was concentrated onto silica gel
  3. washThe column was eluted with 35% acetone in hexanes
  4. additionProduct containing fractions
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-eb189062a09548cea02c0f25f9cffeb5
출처 데이터셋
uspto-grants-2005_03
특허 번호
US06864266B2

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