Phenethylamine → [1-(5-Phenethylcarbamoyl-furan-2-sulfonyl)-piperidin-4-yl]-carbamic acid tert-butyl ester

HRID 337227Notes

Reaction equation

HRID 337227 reaction equation
[CH2:1]([NH2:9])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C[O:11][C:12]([C:14]1[O:15][C:16]([S:19]([N:22]2[CH2:27][CH2:26][CH:25]([NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:24][CH2:23]2)(=[O:21])=[O:20])=[CH:17][CH:18]=1)=O>CO>[C:32]([O:31][C:29](=[O:30])[NH:28][CH:25]1[CH2:26][CH2:27][N:22]([S:19]([C:16]2[O:15][C:14]([C:12](=[O:11])[NH:9][CH2:1][CH2:2][C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=3)=[CH:18][CH:17]=2)(=[O:21])=[O:20])[CH2:23][CH2:24]1)([CH3:35])([CH3:33])[CH3:34]

Participants

4

Reactant 2

HCID 1001PhenethylamineHCID 710601525-(4-tert-Butoxycarbonylamino-piperidine-1-sulfonyl)-furan-2-carboxylic acid methyl ester

Product 1

HCID 71060234[1-(5-Phenethylcarbamoyl-furan-2-sulfonyl)-piperidin-4-yl]-carbamic acid tert-butyl esterYield 96.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
45 °C

Procedure

Phenethylamine (0.5 g, 4.1 mmol) was added in one portion to a stirred solution of 5-(4-tert-butoxycarbonylamino-piperidine-1-sulfonyl)-furan-2-carboxylic acid methyl ester (0.4 g, 1.0 mmol) in methanol (10 ml) at room temperature. The reaction mixture was then heated to 45° C. and stirred at this temperature overnight, after which time the mixture was concentrated. The resulting residue was dissolved in DCM (100 ml), 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 to give the title compound (0.46 g, 94% yield) as a light brown solid which was taken on without further purification. δH (500 MHz, DMSO) 8.71 (t, J=5.79 Hz, 1 H) 7.13-7.38 (m, 8 H) 6.93 (d, J=7.61 Hz, 1 H) 5.75 (s, 1 H) 3.41-3.63 (m, 5 H) 2.66-2.91 (m, 5 H) 1.66-1.87 (m, 2 H) 1.25-1.47 (m, 12 H).

Workup

  1. concentrationafter which time the mixture was concentrated
  2. dissolutionThe resulting residue was dissolved in DCM (100 ml)
  3. washwashed sequentially with HCl (1M solution, 50 ml), NaOH (1M solution, 50 ml) and brine (50 ml)
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e5ab40a0643946b2a0a8bbd481e2ef52
Source dataset
uspto-grants-2014_11
Patent number
US08889716B2

Reaction notes

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