N-(tert-Butoxycarbonyl)-1,5-diaminopentane → Tert-butyl (5-((2-chloroethyl)sulfonamido)pentyl)carbamate

HRID 900221Notes

Reaction equation

HRID 900221 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][NH2:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[Cl:22][CH2:23][CH2:24][S:25](Cl)(=[O:27])=[O:26]>ClCCl>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][NH:14][S:25]([CH2:24][CH2:23][Cl:22])(=[O:27])=[O:26])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 4352N-(tert-Butoxycarbonyl)-1,5-diaminopentaneHCID 8471TriethylamineHCID 15385Ethanesulfonylchloride, 2-chloro-

Product 1

HCID 86594118Tert-butyl (5-((2-chloroethyl)sulfonamido)pentyl)carbamateYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 5-(tert-butoxycarbonylamino)pentylamine (1.00 g, 4.94 mmol) and triethylamine (689 μL g, 4.94 mmol) in dichloromethane (22 mL) at 0° C. was added 2-chloro-1-ethanesulfonyl chloride (470 μL, 4.50 mmol). The reaction mixture was stirred for 2 h at room temperature and then washed with saturated aqueous sodium bicarbonate solution (15 mL). The organic layer was dried (Na2SO4) and the solvent was removed under reduced pressure to give the title compound (100% yield), which was used in the next step without further purification.

Workup

  1. washwashed with saturated aqueous sodium bicarbonate solution (15 mL)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-ce9eb091b7124b28aa25efd417a995a2
Source dataset
uspto-grants-2008_04
Patent number
US07358244B2

Reaction notes

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