Diisopropylethylamine → HCID 71079544, compound

HRID 337221Notes

Reaction equation

HRID 337221 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].[Cl:24][C:25]1[CH:26]=[C:27]([S:34](Cl)(=[O:36])=[O:35])[CH:28]=[CH:29][C:30]=1[N+:31]([O-:33])=[O:32]>C(Cl)Cl>[C:10]([O:14][C:15](=[O:23])[NH:16][CH:17]1[CH2:22][CH2:21][N:20]([S:34]([C:27]2[CH:28]=[CH:29][C:30]([N+:31]([O-:33])=[O:32])=[C:25]([Cl:24])[CH:26]=2)(=[O:36])=[O:35])[CH2:19][CH2:18]1)([CH3:13])([CH3:11])[CH3:12]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 7238334-(N-Boc-amino)piperidineHCID 446307513-Chloro-4-nitrobenzene-1-sulfonyl chloride

Product 1

HCID 71079544HCID 71079544, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Diisopropylethylamine (1.74 ml, 9.98 mmol) was added in one portion to a stirred solution of piperidin-4-yl-carbamic acid tert-butyl ester (0.25 g, 1.25 mmol) in DCM (5 ml) at room temperature. To this mixture was added 3-chloro-4-nitrobenzene sulfonyl chloride (0.32 g, 1.25 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 residue was purified by flash column chromatography (elution: % EtOAc: % Heptane) to give the title compound (0.44 g, 84% yield) as a white solid. δH (500 MHz, DMSO) 7.97-8.12 (m, 3 H) 6.93 (d, J=7.72 Hz, 1 H) 3.64 (d, J=12.77 Hz, 2 H) 3.43 (d, J=3.94 Hz, 2 H) 2.88-3.00 (m, 2 H) 1.78 (d, J=10.40 Hz, 2 H) 1.25-1.46 (m, 11 H). Tr=2.22 min, m/z (ES+) (M+Na)+ 442.

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: % EtOAc: % Heptane)

Sources & evidence

ORD record
ord-4dac61c7795e48758eafb9ce22a40f0b
Source dataset
uspto-grants-2014_11
Patent number
US08889716B2

Reaction notes

Loading…