Pyridine → HCID 86745686, compound

HRID 1030385Notes

Reaction equation

HRID 1030385 reaction equation
[C:1]([O:5][C:6]([CH2:8][O:9][C:10]1[C:11]([CH3:48])=[C:12]2[C:17](=[C:18]([CH3:21])[C:19]=1[CH3:20])[O:16][C:15]([CH2:23][O:24][C:25]1[CH:46]=[CH:45][C:28]([CH2:29][CH:30]3[S:34][C:33](=[O:35])[N:32]([CH2:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[C:31]3=[O:44])=[CH:27][CH:26]=1)([CH3:22])[CH2:14][C:13]2=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:50][OH:51].N1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.CO>[C:1]([O:5][C:6]([CH2:8][O:9][C:10]1[C:11]([CH3:48])=[C:12]2[C:17](=[C:18]([CH3:21])[C:19]=1[CH3:20])[O:16][C:15]([CH2:23][O:24][C:25]1[CH:26]=[CH:27][C:28]([CH2:29][CH:30]3[S:34][C:33](=[O:35])[N:32]([CH2:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[C:31]3=[O:44])=[CH:45][CH:46]=1)([CH3:22])[CH2:14][C:13]2=[N:50][OH:51])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 1049PyridineHCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 19822186HCID 19822186, compound

Product 1

HCID 86745686HCID 86745686, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 0.5 g of t-butyl α-{5-[4-(6-t-butoxycarbonylmethoxy-2,5,7,8-tetramethyl-4-oxochroman-2-ylmethoxy)benzyl]-2,4-dioxothiazolidin-3-yl}acetate (prepared as described in Example 51), 0.2 g of hydroxylamine hydrochloride, 0.2 g of pyridine and 5 ml of methanol was allowed to stand at 25°-30° C. for 5 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 20:1 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 20:1 by volume mixture of benzene and ethyl acetate)

Sources & evidence

ORD record
ord-bb48f719f4264d4b84fe1f449aba201c
Source dataset
uspto-grants-1992_04
Patent number
US05104888

Reaction notes

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