Acetone → HCID 23498447, compound

HRID 1771180Notes

Reaction equation

HRID 1771180 reaction equation
[NH:1]([CH2:5][CH2:6][OH:7])[CH2:2][CH2:3][OH:4].C(=O)([O-])[O-].[Na+].[Na+].CC(C)=O.[CH:18]1[CH:23]=[CH:22][C:21]([CH2:24][O:25][C:26](Cl)=[O:27])=[CH:20][CH:19]=1>O>[OH:4][CH2:3][CH2:2][N:1]([CH2:5][CH2:6][OH:7])[C:26](=[O:27])[O:25][CH2:24][C:21]1[CH:22]=[CH:23][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 8113DiethanolamineHCID 10340Sodium CarbonateHCID 10387Benzyl chloroformate

Product 1

HCID 23498447HCID 23498447, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

A suspension of 2,2′-azanediyldiethanol (7.3 ml, 76.09 mmol), sodium carbonate (18.33 g, 172.94 mmol), acetone (125 ml), and water (125 ml) at 0° C. was treated dropwise over a 15 minute period with Cbz-Cl (10.25 ml, 69.17 mmol). The suspension was stirred an additional 3 hours at 0° C. The suspension was diluted with water (500 ml) and extracted with CHCl3 (2×250 ml). The combined organic extracts were dried over sodium sulfate, filtered and concentrated under reduced pressure. The concentrate was purified by column chromatography (ISCO, eluting with MeOH/DCM, 0→10% over 40 minutes) to give the title compound (12.5 g, yield: 76%).

Workup

  1. extractionextracted with CHCl3 (2×250 ml)
  2. dry with materialThe combined organic extracts were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe concentrate was purified by column chromatography (ISCO, eluting with MeOH/DCM, 0→10% over 40 minutes)

Sources & evidence

ORD record
ord-67bb135a113145b1a92d810b7d5cb1b6
Source dataset
uspto-grants-2016_02
Patent number
US09248140B2

Reaction notes

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