Diglycolamine → HCID 86672801, compound

HRID 1755128Notes

Reaction equation

HRID 1755128 reaction equation
[C:1]([N:8]([CH2:10][C:11]([OH:13])=O)[CH3:9])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[NH2:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][OH:20]>C(O)C>[C:4]([O:3][C:1](=[O:2])[N:8]([CH2:10][C:11](=[O:13])[NH:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][OH:20])[CH3:9])([CH3:5])([CH3:6])[CH3:7]

Participants

4

Reactant 2

HCID 13578DiglycolamineHCID 83692Glycine, N-[(1,1-dimethylethoxy)carbonyl]-N-methyl-

Product 1

HCID 86672801HCID 86672801, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

BOC-sarcosine (900 mg, 4.76 mmol) was dissolved in ethanol (10 ml). 2-(2-Aminoethoxy)ethanol (0.477 ml, 4.76 mmol) and 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride n-hydrate (DMT-MM) (1.79 g, 5.71 mmol) were added and the mixture was stirred at room temperature overnight. The reaction solution was concentrated under reduced pressure, and water was added to the resulting residue, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (dichloromethane-methanol) to give {[2-(2-hydroxy-ethoxy)-ethylcarbamoyl]-methyl}-methyl-carbamic acid tert-butyl ester. This was used in the next reaction without complete purification.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure, and water
  2. additionwas added to the resulting residue
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-90d2941d64c84fd092c7c12955897771
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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