HCID 12798185, compound → HCID 12798192, compound

HRID 1380633Notes

Reaction equation

HRID 1380633 reaction equation
[CH:1]([N:4]([CH2:13][CH:14]1[CH2:18][O:17][C:16]2([CH:26](Br)[CH2:25][CH2:24][C:23]3[N:22]([S:28]([C:31]4[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][CH:32]=4)(=[O:30])=[O:29])[CH:21]=[CH:20][C:19]2=3)[O:15]1)[C:5](=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([CH3:3])[CH3:2]>C1CCN2C(=NCCC2)CC1.CN(C)C=O.C(OCC)(=O)C>[CH:1]([N:4]([C:5](=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:13][CH:14]([OH:15])[CH2:18][O:17][C:16]1[CH:26]=[CH:25][CH:24]=[C:23]2[C:19]=1[CH:20]=[CH:21][N:22]2[S:28]([C:31]1[CH:32]=[CH:33][C:34]([CH3:37])=[CH:35][CH:36]=1)(=[O:30])=[O:29])([CH3:3])[CH3:2]

Participants

5

Reactant 1

HCID 12798185HCID 12798185, compound

Product 1

HCID 12798192HCID 12798192, compoundYield 41%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneSolvent

Conditions

Temperature
85 °C

Procedure

In a three necked flask equipped with a stirrer and a thermometer is added 4'-(N-isopropyl-N-benzoylaminomethyl)-1-p-toluenesulfonyl-5-bromo-4,5,6,7-tetrahydroindole-4-spiro-2'-[1,3]dioxolane (100 parts) and dissolved in a mixture of 1,5-diazabicyclo[5,4,0]-5-undecene (51 parts) and N,N-dimethylformamide (319 parts). After stirring for 24 hours at 85° C., the solution is cooled, diluted with ethyl acetate (300 parts) and washed thrice with water (50 parts). Aqueous washings are combined and washed with ethyl acetate (50 parts). The ethyl acetate solution and ethyl acetate washings are combined, washed with water (30 parts) and dried over anhydrous sodium sulfate (50 parts). After 1 hour, the drying reagent is filtered off and filtrate concentrated to dryness under reduced pressure. Obtained residue (83 parts) is dissolved in ethyl acetate (200 parts), stirred for 30 minutes with active charcoal (10 parts) and filtered through diatomaceous filter-bed. The filtrate concentrated under reduced pressure. The residue is triturated with a small amount of hexane to separate amorphous powder. This is collected by filtration and dried to afford 4-(N-isopropyl-N-benzoyl-3-amino-2-hydroxypropoxy)-1-p-toluenesulfonylindole (35 parts) in 41% yield.

Workup

  1. customIn a three necked flask equipped with a stirrer
  2. temperaturethe solution is cooled
  3. washwashed thrice with water (50 parts)
  4. washwashed with ethyl acetate (50 parts)
  5. washwashed with water (30 parts)
  6. dry with materialdried over anhydrous sodium sulfate (50 parts)
  7. waitAfter 1 hour
  8. filtrationthe drying reagent is filtered off
  9. concentrationfiltrate concentrated to dryness under reduced pressure
  10. dissolutionObtained residue (83 parts) is dissolved in ethyl acetate (200 parts)
  11. stirringstirred for 30 minutes with active charcoal (10 parts)
  12. filtrationfiltered through diatomaceous filter-bed
  13. concentrationThe filtrate concentrated under reduced pressure
  14. customThe residue is triturated with a small amount of hexane
  15. customto separate amorphous powder
  16. filtrationThis is collected by filtration
  17. customdried

Sources & evidence

ORD record
ord-49fb4ffe7ecf46b685d30f8ed2cd30e9
Source dataset
uspto-grants-1986_04
Patent number
US04582905

Reaction notes

Loading…