Hydrochloric Acid → HCID 178475411, compound

HRID 1728497Notes

Reaction equation

HRID 1728497 reaction equation
C(N=C(NC(OCC1C=CC=CC=1)=O)NCCCCC(O)=O)(OCC1C=CC=CC=1)=O.[C:32]([O:35][CH:36]1[N:39]([C:40](=[O:42])[CH3:41])[C:38](=[O:43])[CH:37]1[CH2:44][CH2:45][CH2:46][NH:47][C:48]([NH:60]C(OCC1C=CC=CC=1)=O)=[N:49]C(OCC1C=CC=CC=1)=O)(=[O:34])[CH3:33].[ClH:71].[H][H]>[Pd]>[ClH:71].[C:32]([O:35][CH:36]1[N:39]([C:40](=[O:42])[CH3:41])[C:38](=[O:43])[CH:37]1[CH2:44][CH2:45][CH2:46][NH:47][C:48]([NH2:60])=[NH:49])(=[O:34])[CH3:33]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 178418361HCID 178418361, compoundHCID 178475408HCID 178475408, compoundHCID 178525456HCID 178525456, compound

Product 1

HCID 178475411HCID 178475411, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A methanol/ethyl acetate (1:1/5 mL:5 mL) solution of compound 40 (420 mg, 0.78 mmol) and 1N HCl (0.76 mL), containing 10% palladium on carbon, was shaken in a Parr hydrogenator at 45 psi hydrogen pressure for 2 h. The suspension was filtered through a pad of Celite, and the filtrate was concentrated to afford 170 mg (71%) of the title product as a mixture of trans and cis (2:1) isomers.

Workup

  1. filtrationThe suspension was filtered through a pad of Celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-14ee2da654924fc28ad5999c3bef547f
Source dataset
uspto-grants-1994_07
Patent number
US05326863

Reaction notes

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