Diisopropylethylamine → HCID 71060138, compound

HRID 337203Notes

Reaction equation

HRID 337203 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[S:25]([C:28]1[CH:36]=[CH:35][C:31]([C:32]([OH:34])=[O:33])=[CH:30][CH:29]=1)(=[O:27])=[O:26]>C1COCC1>[C:10]([O:14][C:15]([NH:16][CH:17]1[CH2:22][CH2:21][N:20]([S:25]([C:28]2[CH:29]=[CH:30][C:31]([C:32]([OH:34])=[O:33])=[CH:35][CH:36]=2)(=[O:27])=[O:26])[CH2:19][CH2:18]1)=[O:23])([CH3:13])([CH3:11])[CH3:12]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 823854-(Chlorosulfonyl)benzoic acidHCID 7238334-(N-Boc-amino)piperidine

Product 1

HCID 71060138HCID 71060138, compoundYield 119.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisopropylethylamine (10.9 ml, 62.4 mmol) was added in one portion to a stirred solution of piperidin-4-yl-carbamic acid tert-butyl ester (5.0 g, 20.0 mmol) in THF (150 ml) at room temperature. To this mixture was added 4-(chlorosulfonyl)benzoic acid (5.52 g, 25.0 mmol) portion wise and the mixture was stirred at room temperature under a nitrogen atmosphere for 1 hour. After this time the mixture was concentrated and the resulting residue suspended in HCl (1M solution, 100 ml), the resulting solid precipitate was collected by filtration, washed with water and dried under vacuum give the title compound (9.2 g, 96% yield) as a white solid. Tr=1.28 min m/z (ES+) (M+Na+) 407.

Workup

  1. concentrationAfter this time the mixture was concentrated
  2. filtrationthe resulting solid precipitate was collected by filtration
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-135e1ff799c247f6bc20ce394b02e2da
Source dataset
uspto-grants-2014_11
Patent number
US08889716B2

Reaction notes

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