4-Toluenesulfonyl chloride → 4-tert-Butoxycarbonylamino-1-(toluene-4-sulfonyl)-piperidine-4-carboxylic acid methyl ester

HRID 1949079Notes

Reaction equation

HRID 1949079 reaction equation
[CH3:1][O:2][C:3]([C:5]1([NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1)=[O:4].[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1.CCN(CC)CC.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1([NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:10][CH2:9][N:8]([S:25]([C:22]2[CH:23]=[CH:24][C:19]([CH3:29])=[CH:20][CH:21]=2)(=[O:27])=[O:26])[CH2:7][CH2:6]1)=[O:4]

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 14537079Methyl 4-(((1,1-dimethylethoxy)carbonyl)amino)-4-piperidinecarboxylate

Product 1

HCID 581293884-tert-Butoxycarbonylamino-1-(toluene-4-sulfonyl)-piperidine-4-carboxylic acid methyl esterYield 99.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 0.5 g (1.936 mmol) 4-tert-Butoxycarbonylamino-piperidine-4-carboxylic acid methyl ester, 0.387 g (2.03 mmol) p-toluenesulfonyl chloride and 0.587 g (5.8 mmol) NEt3 in 6 mL DCM was stirred at room temperature over night. DCM and NaHCO3 aq. was added and the organic layer was separated and dried with MgSO4. After evaporation the residue was dried under high vacuum and used without further purification. 0.796 g (95%) of the title compound was obtained as white foam. MS (m/e): 413.2 [(M+H)+].

Workup

  1. customthe organic layer was separated
  2. dry with materialdried with MgSO4
  3. customAfter evaporation the residue
  4. customwas dried under high vacuum
  5. customused without further purification

Sources & evidence

ORD record
ord-5b7b785ab57f488dbd6f9faa4d27451a
Source dataset
uspto-grants-2013_03
Patent number
US08399676B2

Reaction notes

Loading…