N-(tert-Butoxycarbonyl)-1,5-diaminopentane → Tert-butyl 5-(2-nitrophenylsulfonamido)pentylcarbamate

HRID 1486418Notes

Reaction equation

HRID 1486418 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11].[N+:15]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[S:24](Cl)(=[O:26])=[O:25])([O-:17])=[O:16].C(N(C(C)C)CC)(C)C>C(Cl)Cl.C(OC(C)C)(C)C>[N+:15]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[S:24]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8](=[O:14])[O:9][C:10]([CH3:11])([CH3:13])[CH3:12])(=[O:26])=[O:25])([O-:17])=[O:16]

Participants

6

Reactant 3

HCID 4352N-(tert-Butoxycarbonyl)-1,5-diaminopentaneHCID 155402-Nitrobenzenesulfonyl chlorideHCID 81531Diisopropylethylamine

Product 1

HCID 67226448Tert-butyl 5-(2-nitrophenylsulfonamido)pentylcarbamateYield 85%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7914Diisopropyl EtherSolvent

Procedure

To a solution of tert-butyl 5-aminopentylcarbamate 30a (20 g, 99 mmoles) and 2-nitrobenzene-1-sulfonyl chloride 30b (23 g, 1.05 eq) in DCM (200 mL) was added dropwise diisopropyl ethyl amine (19.2 g, 1.5 eq) at 0° C. After stirring at RT overnight, the RM was successively washed with an aqueous solution of citric acid, then brine, dried over magnesium sulfate, filtered and concentrated. Trituration in diisopropyl ether afforded 32.61 g (85% yield) of tert-butyl 5-(2-nitrophenylsulfonamido)pentylcarbamate 30c as a white solid; m/z 388 [M+H]+.

Workup

  1. washthe RM was successively washed with an aqueous solution of citric acid
  2. dry with materialbrine, dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-162d5ed6265444e2806f9906a625ef9b
Source dataset
uspto-grants-2016_08
Patent number
US09427440B2

Reaction notes

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