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

HRID 1171832Notes

Reaction equation

HRID 1171832 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-0532b3520fa44f36b052f7f30efb4a22
Source dataset
uspto-grants-2010_11
Patent number
US07829583B2

Reaction notes

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