Pyridine → HCID 70108837, compound

HRID 1602567Notes

Reaction equation

HRID 1602567 reaction equation
[C:1]([O:5][C:6]([C:8](=[C:13]([OH:53])[C:14](=[O:52])[N:15]([CH:25]([CH3:51])[CH:26]([C:42]1[CH:47]=[CH:46][C:45]2[O:48][CH2:49][O:50][C:44]=2[CH:43]=1)[CH2:27][C:28]1[O:29][C:30]([C:33](=[O:41])[NH:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[CH:31][CH:32]=1)[CH2:16]/[CH:17]=[CH:18]/[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:9][C:10]([OH:12])=[O:11])=[O:7])(C)(C)[CH3:2].C1(/C=C/CNC(C)C(C2C=CC3OCOC=3C=2)CC2OC(C(=O)NC3C=CC=CC=3)=CC=2)C=CC=CC=1.Cl.NO.N1C=CC=CC=1>C(O)C>[CH2:1]([O:5][C:6]([C:8](=[C:13]([OH:53])[C:14](=[O:52])[N:15]([CH:25]([CH3:51])[CH:26]([C:42]1[CH:47]=[CH:46][C:45]2[O:48][CH2:49][O:50][C:44]=2[CH:43]=1)[CH2:27][C:28]1[O:29][C:30]([C:33](=[O:41])[NH:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[CH:31][CH:32]=1)[CH2:16]/[CH:17]=[CH:18]/[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[CH2:9][C:10]([OH:12])=[O:11])=[O:7])[CH3:2]

Participants

6

Reactant 4

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 19611711HCID 19611711, compoundHCID 70279280HCID 70279280, compound

Product 1

HCID 70108837HCID 70108837, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

37 mg of 3-(tert-butoxycarbonyl)-4-hydroxy-4-[N-[(1RS,2RS)-1-methyl-2-(3,4-methylenedioxyphenyl)-3-{5-(phenylcarbamoyl)-2-furyl}propyl]-N-{(E)-3-phenyl-2-propenyl}carbamoyl]-3-butenoic acid prepared by reactions similar to those in Example 1 using N-{(E)-3-phenyl-2-propenyl}-[(1RS,2RS)-1-methyl-2-(3,4-methylenedioxyphenyl)-3-{5-(phenylcarbamoyl)-2-furyl}propyl]amine instead of N-{(E)-3-phenyl-2-propenyl}-[(1R,2R)-1-methyl-2-(3,4-methylenedioxyphenyl)-3-{5-(phenylcarbamoyl)-2-furyl}propyl]amine used as the starting material in Example 1 was dissolved in 10 ml of ethanol and refluxed together with 3.9 mg of hydroxylamine hydrochloride and 9.6 mg of pyridine under heating for 15 hours. The reaction solution was cooled to room temperature and evaporated to dryness under reduced pressure. The residue was purified by silica gel thin layer chromatography [Kieselgel™60F254, Art™5744; chloroform/methanol=10/1] to give 12 mg (yield: 34%) of the title compound as a colorless foamy substance.

Workup

  1. temperatureunder heating for 15 hours
  2. customevaporated to dryness under reduced pressure
  3. customThe residue was purified by silica gel thin layer chromatography [Kieselgel™60F254, Art™5744; chloroform/methanol=10/1]

Sources & evidence

ORD record
ord-d0ede6c1f3dc487c865948090cabd388
Source dataset
uspto-grants-1999_11
Patent number
US05981573

Reaction notes

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