Ethanol → HCID 21263324, compound

HRID 568109Notes

Reaction equation

HRID 568109 reaction equation
[CH3:1][C:2]([CH3:14])([O:4][C:5]([N:7]([CH2:12][CH3:13])[CH2:8][C:9]([OH:11])=[O:10])=[O:6])[CH3:3].[CH2:15](O)[CH3:16].C(N(CC)CC)C>CN(C)C1C=CN=CC=1.ClCCl>[CH2:15]([O:10][C:9](=[O:11])[CH2:8][N:7]([C:5]([O:4][C:2]([CH3:14])([CH3:1])[CH3:3])=[O:6])[CH2:12][CH3:13])[CH3:16]

Participants

6

Reactant 3

HCID 702EthanolHCID 8471TriethylamineHCID 12991451N-(tert-Butoxycarbonyl)-N-ethylglycine

Product 1

HCID 21263324HCID 21263324, compoundYield 89.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a 3° C. solution of 86 g (423 mmole) of N-[(1,1-dimethylethoxy)carbonyl]-N-ethylglycine, 21.4 g (465 mmole) of ethanol and 5.17 g (42.3 mmole) of 4-dimethylaminopyridine in 600 mL of dichloromethane is added 47 g (46.2 mmole) of triethylamine, followed by portionwise addition of 89.1 g (46.5 mmole) of 3-N,N-dimethylaminopropylethylcarbodiimide hydrochloride. The stirred mixture is allowed to warm to ambient temperature and stir overnight. The reaction mixture is washed with water, saturated aqueous sodium bicarbonate and brine, dried over magnesium sulfate, filtered, and concentrated in vacuo to give N-[(1,1-dimethylethoxy)carbonyl]-N-ethylglycine ethyl ester (88 g) as an oil. MS (FAB) 232 (M+H)+.

Workup

  1. washThe reaction mixture is washed with water, saturated aqueous sodium bicarbonate and brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0d80cf81f6d748a696d646d650f81ec3
Source dataset
uspto-grants-2001_01
Patent number
US06180759B2

Reaction notes

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