N-(tert-Butoxycarbonyl)-1,5-diaminopentane → [5-(3-Nitro-benzenesulfonylamino)-pentyl]-carbamic acid-tert-butyl ester

HRID 970412Notes

Reaction equation

HRID 970412 reaction equation
C(N(CC)CC)C.[N+:8]([C:11]1[CH:12]=[C:13]([S:17](Cl)(=[O:19])=[O:18])[CH:14]=[CH:15][CH:16]=1)([O-:10])=[O:9].[C:21]([NH:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][NH2:34])([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22]>CC(C)=O.O>[C:24]([O:23][C:21](=[O:22])[NH:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][NH:34][S:17]([C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([N+:8]([O-:10])=[O:9])[CH:12]=1)(=[O:19])=[O:18])([CH3:27])([CH3:25])[CH3:26]

Participants

6

Reactant 3

HCID 4352N-(tert-Butoxycarbonyl)-1,5-diaminopentaneHCID 8471TriethylamineHCID 84763-Nitrobenzenesulfonyl chloride

Product 1

HCID 12147932[5-(3-Nitro-benzenesulfonylamino)-pentyl]-carbamic acid-tert-butyl ester

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

4.2 ml (30.1 mmol) of triethylamine is added to a solution of 3.21 g (14.5 mmol) of 3-nitrobenzenesulfonyl chloride and 3.0 ml (14.4 mmol) of N-Boc-1,5-diaminopentane in 50 ml of acetone and 15 ml of water. The reaction mixture is stirred for one hour at room temperature. Then, the acetone is drawn off in a rotary evaporator. After water (20 ml) is added, it is extracted with ethyl acetate (2×). The combined organic phases are dried (Na2SO4), filtered and concentrated by evaporation. 5.00 g (12.9 mmol, corresponding to 90% of theory) of the product is obtained as a light yellow oil.

Workup

  1. customThen, the acetone is drawn off in a rotary evaporator
  2. additionAfter water (20 ml) is added
  3. extractionit is extracted with ethyl acetate (2×)
  4. dry with materialThe combined organic phases are dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation
  7. custom5.00 g (12.9 mmol, corresponding to 90% of theory) of the product is obtained as a light yellow oil

Sources & evidence

ORD record
ord-0d7654dcb8f44b0cb734e39245902264
Source dataset
uspto-grants-2007_12
Patent number
US07312225B2

Reaction notes

Loading…