Hydrochloric Acid → HCID 3066299, compound

HRID 1382844Notes

Reaction equation

HRID 1382844 reaction equation
Cl[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[CH2:11][CH2:12][C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[O:21][CH2:22][CH:23]([OH:30])[CH2:24][NH:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:14])[NH:4][CH:3]=1.Cl.C([OH:34])C.[OH-].[Na+]>O>[CH3:27][C:26]([NH:25][CH2:24][CH:23]([OH:30])[CH2:22][O:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[C:13](=[O:14])[CH2:12][CH2:11][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[CH2:2][C:3](=[O:34])[NH:4]2)([CH3:29])[CH3:28]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 21273612HCID 21273612, compound

Product 1

HCID 3066299HCID 3066299, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 6.37 g of the product of Step A, 192 ml of N hydrochloric acid and 192 ml of ethanol was stirred for 17 hours at room temperature and was then diluted with water. The mixture was made alkaline by addition of sodium hydroxide and was extracted with ethyl acetate. The organic phase was washed with water, dried and evaporated to dryness under reduced pressure. The residue was chromatographed over silica and eluted with a 6-3-1 chloroform-acetone-triethylamine mixture to obtain 2.32 g of 1,3-dihydro-4-[3-[2-[3-(1,1-dimethylethylamino)-2-hydroxypropoxy]-phenyl]-3-oxopropyl]-2H-indol-2-one.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe organic phase was washed with water
  3. customdried
  4. customevaporated to dryness under reduced pressure
  5. customThe residue was chromatographed over silica
  6. washeluted with a 6-3-1 chloroform-acetone-triethylamine mixture

Sources & evidence

ORD record
ord-326b133c941049f6a05c29d34c123a84
Source dataset
uspto-grants-1989_02
Patent number
US04808609

Reaction notes

Loading…