Water → (S)-2-((tert-butoxycarbonyl)amino)butyl methanesulfonate

HRID 576693Notes

Reaction equation

HRID 576693 reaction equation
[C:1]([O:5][C:6](=[O:13])[NH:7][C@@H:8]([CH2:11][CH3:12])[CH2:9][OH:10])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23].O>CCOCC>[CH3:21][S:22]([O:10][CH2:9][C@@H:8]([NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:13])[CH2:11][CH3:12])(=[O:24])=[O:23]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 11263954tert-butyl N-[(2S)-1-hydroxybutan-2-yl]carbamate

Product 1

HCID 89537961(S)-2-((tert-butoxycarbonyl)amino)butyl methanesulfonateYield 100.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To an ice cold solution of (S)-tert-butyl(1-hydroxybutan-2-yl)carbamate (9.5 g, 50 mmol) and triethylamine (10.5 mL, 75 mmol) in ether (200 mL) was added methanesulfonyl chloride (4.0 mL, 50 mmol). After 1 h, water was added, and the resulting mixture was extracted with DCM, dried (Na2SO4), filtered, and concentrated to give an oil (13.4 g, 100%) which was used directly without further purification.

Workup

  1. extractionthe resulting mixture was extracted with DCM
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9d3a79e277f74b61820f0c08d482b8bd
Source dataset
uspto-grants-2015_05
Patent number
US09040534B2

Reaction notes

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