Benzyl chloroformate → [4-(4-Acryloylamino-piperidine-1-sulfonyl)-phenyl]carbamic acid benzyl ester

HRID 337202Notes

Reaction equation

HRID 337202 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][CH:14]([NH:17][C:18](=[O:21])[CH:19]=[CH2:20])[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.Cl[C:32]([O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:33]>C1COCC1.C(Cl)Cl>[CH2:35]([O:34][C:32](=[O:33])[NH:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]2[CH2:12][CH2:13][CH:14]([NH:17][C:18](=[O:21])[CH:19]=[CH2:20])[CH2:15][CH2:16]2)(=[O:9])=[O:10])=[CH:6][CH:7]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

6

Reactant 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 71618273N-[1-(4-Amino-benzenesulfonyl)-piperidin-4-yl]-acrylamide

Product 1

HCID 71449433[4-(4-Acryloylamino-piperidine-1-sulfonyl)-phenyl]carbamic acid benzyl esterYield 34%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

N-[1-(4-Amino-benzenesulfonyl)-piperidin-4-yl]-acrylamide (0.09 g, 0.3 mmol) was dissolved in THF (5 ml). To this was added diisopropylethylamine (0.1 ml, 0.6 mmol) in one portion followed by the drop wise addition of benzyl chloroformate (0.05 ml, 0.33 mmol) and the mixture was stirred at room temperature under a nitrogen atmosphere for 3 hours. After this time the mixture was diluted with DCM (100 ml) and washed sequentially with HCl (1M solution, 50 ml), NaOH (1M solution, 50 ml) and brine (50 ml). The organic layer was separated, dried (MgSO4), filtered and concentrated. The resulting residue was purified by flash column chromatography (elution: 100% EtOAc) to give the title compound (0.04 g, 34% yield) as a white powder.

Workup

  1. washwashed sequentially with HCl (1M solution, 50 ml), NaOH (1M solution, 50 ml) and brine (50 ml)
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting residue was purified by flash column chromatography (elution: 100% EtOAc)

Sources & evidence

ORD record
ord-c8d40014bebf4708ad8cc61cd3084959
Source dataset
uspto-grants-2014_11
Patent number
US08889716B2

Reaction notes

Loading…