p-Toluenesulfonic acid → HCID 86625768, compound

HRID 2077274Notes

Reaction equation

HRID 2077274 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][C:15](=[O:24])[NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(C)C=CC(S(O)(=O)=O)=CC=1>ClC1C=CC=C(Cl)C=1.ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][C:15]1[O:24][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N:16]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 86625767HCID 86625767, compound

Product 1

HCID 86625768HCID 86625768, compoundYield 42.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 109431,3-DichlorobenzeneSolvent

Procedure

(RS)-2-[(2-Hydroxy-phenylcarbamoyl)-methyl]-piperidine-1-carboxylic acid tert butyl ester (1.25 g), 4-toluenesulphonic acid (0.07 g) and 4-N,N-dimethylaminopyridine (0.023 g) were combined in 1,3-dichlorobenzene (30 ml) and the mixture boiled for 48 h. The mixture was diluted with dichloromethane and washed with water. The organic phase was dried (MgSO4) and solvent removed at reduced pressure. The residue was column chromatographed (silica gel, 0→1% methanol in dichloromethane) to give the title compound (0.50 g)

Workup

  1. washwashed with water
  2. dry with materialThe organic phase was dried (MgSO4) and solvent
  3. customremoved at reduced pressure
  4. customchromatographed (silica gel, 0→1% methanol in dichloromethane)

Sources & evidence

ORD record
ord-47393ea7e286405ea42ceb7edffd44d1
Source dataset
uspto-grants-2011_04
Patent number
US07928124B2

Reaction notes

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