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

反応式

HRID 983457 の反応式
[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]

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒2 回HCID 11430Potassium Carbonate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-eb189062a09548cea02c0f25f9cffeb5
出典データセット
uspto-grants-2005_03
特許番号
US06864266B2

関連ノート

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