Water → Carbamic acid, N-methyl-N-[2-oxo-2-(2-propen-1-ylamino)ethyl]-, 1,1-dimethylethyl ester

HRID 1755103Notes

Reaction equation

HRID 1755103 reaction equation
[CH2:1]([NH2:4])[CH:2]=[CH2:3].[C:5]([N:12]([CH2:14][C:15](O)=[O:16])[CH3:13])([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].C(=O)(O)[O-].[Na+].O>C(O)C>[C:8]([O:7][C:5](=[O:6])[N:12]([CH2:14][C:15](=[O:16])[NH:4][CH2:1][CH:2]=[CH2:3])[CH3:13])([CH3:11])([CH3:9])[CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 7853AllylamineHCID 83692Glycine, N-[(1,1-dimethylethoxy)carbonyl]-N-methyl-HCID 516892Sodium Bicarbonate

Product 1

HCID 86672796Carbamic acid, N-methyl-N-[2-oxo-2-(2-propen-1-ylamino)ethyl]-, 1,1-dimethylethyl esterYield 62%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Allylamine (0.377 ml, 5.03 mmol) and 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride n-hydrate (DMT-MM) (1.89 g, 6.04 mmol) were added to a solution of Boc-sarcosine (1.0 g, 5.29 mmol) in ethanol, and the mixture was stirred at room temperature for 18 hours. A saturated aqueous sodium bicarbonate solution and water were added to the reaction solution, followed by extraction with ether. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure to give allylcarbamoylmethyl-methyl-carbamic acid tert-butyl ester (712 mg).

Workup

  1. extractionfollowed by extraction with ether
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7cd5612a1e484db59fb3aa58a2e9b8b4
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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