Diisopropylamine → HCID 21078400, compound

HRID 1374899Notes

Reaction equation

HRID 1374899 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([O:10][CH:11]([CH2:22][CH3:23])[C:12]([NH:14][C:15]([CH3:21])([CH3:20])[C:16]#[C:17][CH2:18][CH3:19])=[O:13])[CH:7]=[N:8][CH:9]=1)([OH:3])=O.[CH:24]([NH:27][CH:28]([CH3:30])[CH3:29])([CH3:26])[CH3:25]>CN(C)C=O.O>[CH:24]([N:27]([CH:28]([CH3:30])[CH3:29])[C:1]([C:4]1[CH:5]=[C:6]([O:10][CH:11]([CH2:22][CH3:23])[C:12]([NH:14][C:15]([CH3:21])([CH3:20])[C:16]#[C:17][CH2:18][CH3:19])=[O:13])[CH:7]=[N:8][CH:9]=1)=[O:3])([CH3:26])[CH3:25]

Participants

5

Reactant 2

HCID 7912DiisopropylamineHCID 21078377HCID 21078377, compound

Product 1

HCID 21078400HCID 21078400, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The product from Stage 3 (0.22 g) in dry N,N-dimethylformamide (5 ml) containing N-(3-(dimethylaminopropyl))-N′-ethylcarbodiimide hydrochloride (0.14 g) was stirred at ambient temperature and treated dropwise with diisopropylamine (0.20 ml). The mixture was stirred at ambient temperature for 2 hours, diluted with water, extracted with diethyl ether (three times) and the organic fractions combined, washed with aqueous sodium hydrogen carbonate (twice), water (twice) and dried over magnesium sulphate. The solvent was evaporated under reduced pressure and the residual gum was fractionated by chromatography (silica; ethyl acetate) to give the required product as a colourless gum, 0.06 g.

Workup

  1. stirringThe mixture was stirred at ambient temperature for 2 hours
  2. extractionextracted with diethyl ether (three times)
  3. washwashed with aqueous sodium hydrogen carbonate (twice), water (twice) and
  4. dry with materialdried over magnesium sulphate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-251855bfca264b73960277db063dfbfb
Source dataset
uspto-grants-2007_01
Patent number
US07166621B2

Reaction notes

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