HCID 23277613, compound → HCID 23277598, compound

HRID 1605500Notes

Reaction equation

HRID 1605500 reaction equation
[N+:1]([C:4]1[C:12]([CH2:13][CH2:14][CH:15]([CH3:43])[CH:16]([OH:42])[CH:17]([CH3:41])[C:18](=[O:40])[CH:19]([CH2:38][CH3:39])[CH:20]2[CH:24]([CH3:25])[CH2:23][C:22]([CH2:36][CH3:37])([CH:26]3[CH2:31][CH2:30][C:29]([CH2:33][CH3:34])([OH:32])[CH:28]([CH3:35])[O:27]3)[O:21]2)=[C:8]([C:9]([OH:11])=[O:10])[C:7]([OH:44])=[C:6]([CH3:45])[CH:5]=1)([O-])=O.[H][H]>C(O)C.[Ni]>[NH2:1][C:4]1[C:12]([CH2:13][CH2:14][CH:15]([CH3:43])[CH:16]([OH:42])[CH:17]([CH3:41])[C:18](=[O:40])[CH:19]([CH2:38][CH3:39])[CH:20]2[CH:24]([CH3:25])[CH2:23][C:22]([CH2:36][CH3:37])([CH:26]3[CH2:31][CH2:30][C:29]([CH2:33][CH3:34])([OH:32])[CH:28]([CH3:35])[O:27]3)[O:21]2)=[C:8]([C:9]([OH:11])=[O:10])[C:7]([OH:44])=[C:6]([CH3:45])[CH:5]=1

Participants

5

Reactant 2

HCID 23277613HCID 23277613, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 23277598HCID 23277598, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A solution of 5.0 g. (7.6 millimole) of 5-nitro-3-methyl-6-{7-ethyl-4-hydroxy-3,5-dimethyl-6-oxo-7-[5-ethyl-3-methyl-5-(5-ethyl-5-hydroxy-6-methyl-2-tetrahydropyranyl)-2-tetrahydrofuryl]-heptyl}salicylic acid in ethanol (450 ml.) was hydrogenated over 2 g. of Raney-nickel with an uptake of 22.2 mm. of hydrogen. The reaction was filtered (over N2) and 17.2 ml. of N HCl was added. The solvent was removed under reduced pressure, and the residue was crystallized from aqueous acetone to give 5-amino-3-methyl-6-{7-ethyl-4-hydroxy-3,5-dimethyl-6-oxo-7-[5-ethyl-3-methyl-5-(5-ethyl-5-hydroxy-6-methyl-2-tetrahydropyranyl)-2-tetrahydrofuryl]-heptyl}salicylic acid, m.p. 223°-225°[α]D25 +17.92° (1%, MeOH).

Workup

  1. filtrationThe reaction was filtered (over N2) and 17.2 ml
  2. additionof N HCl was added
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was crystallized from aqueous acetone

Sources & evidence

ORD record
ord-f9f1117c4622404caa1290c2fc25ceee
Source dataset
uspto-grants-1976_04
Patent number
US03950320

Reaction notes

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