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

Reaction equation

HRID 983457 reaction equation
[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]

Participants

5

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolvent2×HCID 11430Potassium CarbonateSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-eb189062a09548cea02c0f25f9cffeb5
Source dataset
uspto-grants-2005_03
Patent number
US06864266B2

Linked notes

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