Pyridine → HCID 86745685, compound

HRID 1030384Notes

Reaction equation

HRID 1030384 reaction equation
[OH:1][C:2]1[C:3]([CH3:40])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([CH2:15][O:16][C:17]1[CH:38]=[CH:37][C:20]([CH2:21][CH:22]3[S:26][C:25](=[O:27])[N:24]([CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[C:23]3=[O:36])=[CH:19][CH:18]=1)([CH3:14])[CH2:6][C:5]2=O.Cl.[NH2:42][OH:43].N1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.CO>[OH:1][C:2]1[C:3]([CH3:40])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([CH2:15][O:16][C:17]1[CH:38]=[CH:37][C:20]([CH2:21][CH:22]3[S:26][C:25](=[O:27])[N:24]([CH2:28][C:29]([O:31][C:32]([CH3:33])([CH3:34])[CH3:35])=[O:30])[C:23]3=[O:36])=[CH:19][CH:18]=1)([CH3:14])[CH2:6][C:5]2=[N:42][OH:43]

Participants

7

Reactant 4

HCID 1049PyridineHCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 19822247HCID 19822247, compound

Product 1

HCID 86745685HCID 86745685, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 0.5 g of t-butyl α-{5-[4-(6-hydroxy-2,5,7,8-tetramethyl-4-oxochroman-2-ylmethoxy)benzyl]-2,4-dioxothiazolidin-3yl}acetate (prepared as described in Example 49), 0.25 g of hydroxylamine hydrochloride, 0.25 g of pyridine and 5 ml of methanol was allowed to stand t 25°-30° C. for 2 days. Ethyl acetate and an aqueous solution of potassium carbonate were added to the mixture, and the organic layer was separated. The organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off and the residue was subjected to silica gel column chromatography (eluted with a 9:1 by volume mixture of benzene and ethyl acetate) to obtain the title compound.

Workup

  1. customthe organic layer was separated
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. distillationThe solvent was distilled off
  4. washeluted with a 9:1 by volume mixture of benzene and ethyl acetate)

Sources & evidence

ORD record
ord-6daeecf88aba4c3ebed33d8fb03e42f5
Source dataset
uspto-grants-1992_04
Patent number
US05104888

Reaction notes

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