Diisopropylethylamine → 5-(4-tert-Butoxycarbonylamino-piperidine-1-sulfonyl)-furan-2-carboxylic acid methyl ester

HRID 337226Notes

Reaction equation

HRID 337226 reaction equation
C(N(C(C)C)CC)(C)C.[C:10]([O:14][C:15](=[O:23])[NH:16][CH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)([CH3:13])([CH3:12])[CH3:11].[CH3:24][O:25][C:26]([C:28]1[O:29][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:31][CH:32]=1)=[O:27]>C(Cl)Cl>[CH3:24][O:25][C:26]([C:28]1[O:29][C:30]([S:33]([N:20]2[CH2:21][CH2:22][CH:17]([NH:16][C:15]([O:14][C:10]([CH3:13])([CH3:11])[CH3:12])=[O:23])[CH2:18][CH2:19]2)(=[O:35])=[O:34])=[CH:31][CH:32]=1)=[O:27]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 7238334-(N-Boc-amino)piperidineHCID 2736845Methyl 5-(Chlorosulfonyl)-2-Furoate

Product 1

HCID 710601525-(4-tert-Butoxycarbonylamino-piperidine-1-sulfonyl)-furan-2-carboxylic acid methyl esterYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Diisopropylethylamine (0.75 ml, 4.45 mmol) was added in one portion to a stirred solution of piperidin-4-yl-carbamic acid tert-butyl ester (0.45 g, 2.26 mmol) in DCM (5 ml) at room temperature. To this mixture was added 5-chlorosulfonyl-furan-2-carboxylic acid methyl ester (0.5 g, 2.26 mmol) in one portion and the mixture was stirred at room temperature under a nitrogen atmosphere for 1 hour. 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 solid was collected by filtration, washed with diethyl ether and dried under vacuum to give the title compound (0.76 g, 88% yield) as an off-white solid. Tr=1.98 min, m/z (ES+) (M+Na)+ 411.

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. filtrationThe resulting solid was collected by filtration
  7. washwashed with diethyl ether
  8. customdried under vacuum

Sources & evidence

ORD record
ord-9b6392ce081241b3b512d6fd7f6ecf7c
Source dataset
uspto-grants-2014_11
Patent number
US08889716B2

Reaction notes

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