Methanesulfonyl chloride → Methanesulfonic acid 5-Boc-amino-pentyl ester

HRID 234487Notes

Reaction equation

HRID 234487 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][OH:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:15][S:16](Cl)(=[O:18])=[O:17]>N1C=CC=CC=1>[CH3:15][S:16]([O:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])(=[O:18])=[O:17]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 44561365-(Boc-amino)-1-pentanol

Product 1

HCID 17750371Methanesulfonic acid 5-Boc-amino-pentyl esterYield 98.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 28.6 g of 5-(tert-butoxycarbonylamino)pentan-1-ol in 100 ml of pyridine is cooled to 0° C. and 16.2 g of methanesulfonyl chloride are added dropwise in 3 hours at 0° C. The reaction mixture is stirred overnight at RT and concentrated under vacuum. The residue is taken up with water and extracted with AcOEt, the organic phase is washed three times with water, three times with a 5% solution of potassium hydrogensulfate, three times with water and with a saturated solution of NaCl and dried over sodium sulfate and the solvent is evaporated off under vacuum to give 39 g of the expected product, which is used as such in the next step.

Workup

  1. concentrationconcentrated under vacuum
  2. extractionextracted with AcOEt
  3. washthe organic phase is washed three times with water, three times with a 5% solution of potassium hydrogensulfate, three times with water
  4. dry with materialwith a saturated solution of NaCl and dried over sodium sulfate
  5. customthe solvent is evaporated off under vacuum

Sources & evidence

ORD record
ord-38853f5a3d3e426ca151acbc21a747a0
Source dataset
uspto-grants-1997_01
Patent number
US05594023

Reaction notes

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