Diethanolamine → HCID 23498447, compound

HRID 1883161Notes

Reaction equation

HRID 1883161 reaction equation
[NH:1]([CH2:5][CH2:6][OH:7])[CH2:2][CH2:3][OH:4].[CH2:8]([O:15][C:16](OC1CC(=O)NC1=O)=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1.O>[C:16]([N:1]([CH2:5][CH2:6][OH:7])[CH2:2][CH2:3][OH:4])([O:15][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:17]

Participants

6

Reactant 3

HCID 8113DiethanolamineHCID 10340Sodium CarbonateHCID 22140026HCID 22140026, compound

Product 1

HCID 23498447HCID 23498447, compoundYield 88.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution of diethanolamine (1.9 ml, 20 mmol) in 50 ml of THF was added benzyloxycarbonyloxysuccinimide (5.0 g, 20 mmol) followed by the slow addition of a solution of sodium carbonate (3.2 g, 30 mmol) in 50 ml of water. The reaction was stirred at 0° C. for 2 hours, diluted with 50 ml of water, and the majority of the THF was removed under vacuum. The reaction mixture was extracted with ethyl acetate (2×75 ml), washed with brine and dried over sodium sulfate. The solvent was concentrated and the residue was purified by SiO2 chromatography (250 g SiO2, 8% MeOH/methylene chloride) to give N-Cbz-diethanolamine (4.25 g) as a clear oil.

Workup

  1. customthe majority of the THF was removed under vacuum
  2. extractionThe reaction mixture was extracted with ethyl acetate (2×75 ml)
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationThe solvent was concentrated
  6. customthe residue was purified by SiO2 chromatography (250 g SiO2, 8% MeOH/methylene chloride)

Sources & evidence

ORD record
ord-57a446727e0c43c6b1b81bf7201da705
Source dataset
uspto-grants-2004_07
Patent number
US06759428B2

Reaction notes

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