Triethylamine → 3-((tert-Butoxycarbonyl)(isobutyl)amino)-propyl methanesulfonate

HRID 58999Notes

Reaction equation

HRID 58999 reaction equation
[C:1]([O:5][C:6](=[O:16])[N:7]([CH2:12][CH2:13][CH2:14][OH:15])[CH2:8][CH:9]([CH3:11])[CH3:10])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>C(Cl)Cl>[CH3:24][S:25]([O:15][CH2:14][CH2:13][CH2:12][N:7]([C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:16])[CH2:8][CH:9]([CH3:11])[CH3:10])(=[O:27])=[O:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 117844580tert-Butyl(3-hydroxypropyl)(isobutyl)carbamate

Product 1

HCID 1177045153-((tert-Butoxycarbonyl)(isobutyl)amino)-propyl methanesulfonateYield 64.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl(3-hydroxypropyl)(isobutyl)carbamate (0.73 g, 3.15), triethylamine (0.64 g, 6.30 mmol) and CH2Cl2 (30 mL) were added to a round-bottom flask. To the solution was added methanesulfonyl chloride (0.54 g, 4.72 mmol) and the reaction mixture was stirred for 5 h. The reaction mixture was concentrated under reduced pressure and purified by column chromatography (hexanes/EtOAC) to afford the desired product (0.63 g, 64%) as a yellow oil.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. custompurified by column chromatography (hexanes/EtOAC)

Sources & evidence

ORD record
ord-fe9b899f1bc840899625d0c05c6dcda8
Source dataset
uspto-grants-2016_09
Patent number
US09439433B2

Reaction notes

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