Triethylamine → (R)-2-((tert-butoxycarbonyl)amino)propyl methanesulfonate

HRID 2220647Notes

Reaction equation

HRID 2220647 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[C:6]([O:10][C:11]([NH:13][C@H:14]([CH3:17])[CH2:15][OH:16])=[O:12])([CH3:9])([CH3:8])[CH3:7].C(N(CC)CC)C>C(Cl)Cl>[CH3:1][S:2]([O:16][CH2:15][C@H:14]([NH:13][C:11]([O:10][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:12])[CH3:17])(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 13200309tert-butyl N-((2R)-1-hydroxypropan-2-yl)carbamate

Product 1

HCID 14427185(R)-2-((tert-butoxycarbonyl)amino)propyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (0.64 mL) was added dropwise to an ice-cooled mixture of (R)-(+)-2-(tert-butoxycarbonylamino)-propanol (1.31 g) and triethylamine (1.6 mL) in methylene chloride (20 mL) with stirring, and the mixture was stirred at that temperature for 1 hr. The reaction mixture was washed successively with water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to afford the title compound (1.93 g).

Workup

  1. temperaturecooled
  2. stirringthe mixture was stirred at that temperature for 1 hr
  3. washThe reaction mixture was washed successively with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-fcaba5752dee4b9ea0c3b341aba2b82f
Source dataset
uspto-grants-2008_08
Patent number
US07417169B2

Reaction notes

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