Hydrochloric Acid → HCID 178448142, compound

HRID 1737073Notes

Reaction equation

HRID 1737073 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[CH2:14][CH2:13][C@H:12]([OH:15])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1)#[N:2].[CH2:16]([C@@H:19]1[CH2:23][C@@H:22]([CH2:24]OS(C)(=O)=O)[N:21]([CH2:30][CH2:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:20]1=[O:39])[CH:17]=[CH2:18].[OH-].[K+].Cl>O>[CH2:16]([C@@H:19]1[CH2:23][C@@H:22]([CH2:24][O:15][C@H:12]2[CH2:13][CH2:14][C@H:9]([C:6]3[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=3)[CH2:10][CH2:11]2)[N:21]([CH2:30][CH2:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:20]1=[O:39])[CH:17]=[CH2:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 57075773HCID 57075773, compoundHCID 178509806HCID 178509806, compound

Product 1

HCID 178448142HCID 178448142, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.73 g of trans-4-(4-cyanophenyl)cyclohexanol, 2.8 g of (3R,5S)-3-allyl-5-[(methanesulphonyl)oxymethyl]-1-(3-phenylpropyl)-2-pyrrolidinone, 2.5 ml of 60% aqueous potassium hydroxide solution and 0.3 g of polyethyleneglycol-750 monomethylether (bound to polystyrene-1% divinylbenzene) are stirred for 24 hours at 45° C. Ice and water are added to the mixture, it is acidified with hydrochloric acid and extracted with ethyl acetate. The organic phase is dried with sodium sulphate, concentrated by evaporation and the residue is chromatographed over a silica gel column with petroleum ether/ethyl acetate (2:1). 0.4 g (24% of theory) of product are obtained. Rf value: 0.61 (silica gel; petroleum ether/ethyl acetate 12:1) Calculated: C 78.91 H 7.95 N 6.14 Found: 78.88 8.13 6.10

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic phase is dried with sodium sulphate
  3. concentrationconcentrated by evaporation
  4. customthe residue is chromatographed over a silica gel column with petroleum ether/ethyl acetate (2:1)
  5. custom0.4 g (24% of theory) of product are obtained

Sources & evidence

ORD record
ord-23d62eab8e464c488cf87804f7707af5
Source dataset
uspto-grants-1996_07
Patent number
US05541343

Reaction notes

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