Diisopropylethylamine → HCID 19045270, compound

HRID 1781368Notes

Reaction equation

HRID 1781368 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:7]=[CH:8][C:9]2[O:26][C:13]3([CH2:18][CH2:17][CH2:16][N:15](CC4C=CC=CC=4)[CH2:14]3)[CH2:12][C:11](=[O:27])[C:10]=2[CH:28]=1)(=[O:4])=[O:3].C(N(C(C)C)CC)(C)C.[Cl:38]C(OC(Cl)C)=O.C(=O)(O)[O-].[Na+]>ClC(Cl)C>[ClH:38].[CH3:1][S:2]([NH:5][C:6]1[CH:7]=[CH:8][C:9]2[O:26][C:13]3([CH2:18][CH2:17][CH2:16][NH:15][CH2:14]3)[CH2:12][C:11](=[O:27])[C:10]=2[CH:28]=1)(=[O:3])=[O:4]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 5213051-Chloroethyl chloroformateHCID 19045367HCID 19045367, compound

Product 1

HCID 19045270HCID 19045270, compoundYield 67.7%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

A solution of 7 g (17.47 mmols) of 6-methanesulfonamido-1'-benzyl-3,4-dihydrospiro-[(2H)-1-benzopyran-2,3'-piperidine]-4-one in 250 mL dichloroethane was treated with 5.6 g (43.7 mmole) of diisopropylethylamine, and 6.24 g (43.7 mmoles) of 1-chloroethyl chloroformate. The reaction was stirred at room temperature for 24 hours and then poured into 500 mL saturated sodium bicarbonate, and extracted with ethyl acetate. The ethyl acetate layers were washed with dilute acid to remove excess diisopropylethylamine. The ethyl acetate solution was then dried over MgSO4, filtered and concentrated in vacuo. The crude material was dissolved in 250 mL CH3OH and heated to reflux for 24 hours. The reaction mixture was cooled to room temperature and the solid collected by filtration to give 4.1 g of product, mp=290° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layers were washed
  3. additionwith dilute acid
  4. customto remove excess diisopropylethylamine
  5. dry with materialThe ethyl acetate solution was then dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. dissolutionThe crude material was dissolved in 250 mL CH3OH
  9. temperatureheated
  10. temperatureto reflux for 24 hours
  11. temperatureThe reaction mixture was cooled to room temperature
  12. filtrationthe solid collected by filtration

Sources & evidence

ORD record
ord-6aeb04d026c546f9b1095e74fc25312b
Source dataset
uspto-grants-1997_05
Patent number
US05633247

Reaction notes

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