Piperidine → (R)-4-thiocarbamoyl-1-(4-trifluoromethoxy-benzenesulfonyl)-piperazine-2-carboxylic acid benzyl ester

HRID 908592Notes

Reaction equation

HRID 908592 reaction equation
Cl.[CH2:2]([O:9][C:10]([C@H:12]1[CH2:17][NH:16][CH2:15][CH2:14][N:13]1[S:18]([C:21]1[CH:26]=[CH:25][C:24]([O:27][C:28]([F:31])([F:30])[F:29])=[CH:23][CH:22]=1)(=[O:20])=[O:19])=[O:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.C1C2C(COC([N:56]=[C:57]=[S:58])=O)C3C(=CC=CC=3)C=2C=CC=1.N1CCCCC1>C(Cl)(Cl)Cl>[CH2:2]([O:9][C:10]([C@H:12]1[CH2:17][N:16]([C:57](=[S:58])[NH2:56])[CH2:15][CH2:14][N:13]1[S:18]([C:21]1[CH:26]=[CH:25][C:24]([O:27][C:28]([F:31])([F:29])[F:30])=[CH:23][CH:22]=1)(=[O:20])=[O:19])=[O:11])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 8082PiperidineHCID 8471TriethylamineHCID 4154759Fmoc isothiocyanateHCID 67408219(R)-1-(4-trifluoromethoxy-benzenesulfonyl)-piperazine-2-carboxylic acid benzyl ester hydrochloride

Product 1

HCID 59703783(R)-4-thiocarbamoyl-1-(4-trifluoromethoxy-benzenesulfonyl)-piperazine-2-carboxylic acid benzyl esterYield 78.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of the compound (2.58 g) obtained in Step 3 in chloroform (26 ml) was added, with stirring at room temperature, triethylamine (896 μl), and 9-fluorenylmethoxycarbonyl isothiocyanate (1.66 g) was added. After stirring overnight at room temperature, piperidine (1.11 ml) was added. After stirring overnight at room temperature, the reaction mixture was concentrated under reduced pressure, and purified by column chromatography (5% methanol/chloroform) to give the title compound (2.12 g).

Workup

  1. stirringAfter stirring overnight at room temperature
  2. stirringAfter stirring overnight at room temperature
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. custompurified by column chromatography (5% methanol/chloroform)

Sources & evidence

ORD record
ord-f14641bff0084f19b54c8e6ac3e16b90
Source dataset
uspto-grants-2011_09
Patent number
US08017612B2

Reaction notes

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