Triethylamine → 2-tert-Butoxycarbonylaminopropyl methanesulfonate

HRID 1260526Notes

Reaction equation

HRID 1260526 reaction equation
[OH:1][CH2:2][CH:3]([NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[CH3:4].C(N(CC)CC)C.[CH3:20][S:21](Cl)(=[O:23])=[O:22].C(=O)(O)[O-].[Na+]>CN(C)C1C=CN=CC=1.C1COCC1.C(OCC)(=O)C>[CH3:20][S:21]([O:1][CH2:2][CH:3]([NH:5][C:6]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:12])[CH3:4])(=[O:23])=[O:22]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 545701tert-butyl N-(1-hydroxypropan-2-yl)carbamate

Product 1

HCID 144271842-tert-Butoxycarbonylaminopropyl methanesulfonate

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl (2-hydroxy-1-methylethyl)carbamate (2.8 g, 15.98 mmol), triethylamine (4.44 ml, 3.23 mmol) and 4-dimethylaminopyridine (195 mg, 1.59 mmol) were dissolved in 135 ml of THF. Methanesulfonyl chloride (1.3 ml, 16.78 mmol) was added dropwise on an ice bath, and the reaction mixture was stirred for 3 h and warmed to room temperature. Following addition of ethyl acetate and sodium bicarbonate solution, the organic phase was separated off and concentrated. Yield: 3.97 g (98%).

Workup

  1. customthe organic phase was separated off
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-9a6a5320cdd742c995a22b397ad94fdb
Source dataset
uspto-grants-2013_06
Patent number
US08470841B2

Reaction notes

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