Water → HCID 57187157, compound

HRID 279050Notes

Reaction equation

HRID 279050 reaction equation
[OH:1]OS([O-])=O.[K+].[CH3:7][S:8][C:9]1[CH:10]=[CH:11][C:12]2[N:13]([C:15]([C:18]([C:20]3[CH:25]=[CH:24][C:23]([N:26]4[CH2:30][C@H:29]([CH2:31][NH:32][C:33](=[O:35])[CH3:34])[O:28][C:27]4=[O:36])=[CH:22][CH:21]=3)=[O:19])=[CH:16][N:17]=2)[CH:14]=1.[OH2:37]>CCO>[CH3:7][S:8]([C:9]1[CH:10]=[CH:11][C:12]2[N:13]([C:15]([C:18]([C:20]3[CH:21]=[CH:22][C:23]([N:26]4[CH2:30][C@H:29]([CH2:31][NH:32][C:33](=[O:35])[CH3:34])[O:28][C:27]4=[O:36])=[CH:24][CH:25]=3)=[O:19])=[CH:16][N:17]=2)[CH:14]=1)(=[O:1])=[O:37]

Participants

5

Reactant 3

HCID 962WaterHCID 23707502Potassium hydroxy sulfiteHCID 57194150HCID 57194150, compound

Product 1

HCID 57187157HCID 57187157, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of Oxone (0.356 g. 0.579 mM) in water (2.5 ml) was added to a stirred suspension of the title product from Example 37 (0.117 g. 0.276 mM) in EtOH (10 ml) and the mixture heated at gentle reflux for 2.75 hours. The mixture was allowed to cool. The solid which precipitated was filtered, washed with water and ether to give the title compound (0.1 09 g). MS: 457 (MH+); NMR(250 MHz) 1.83 (3H, s); 3.38 (3H, s); 3.45 (2H, t); 3.85 (1H, m); 4.23 (1H, t); 4.79 (1H, m); 7.78 (2H, d); 8.0 (2H, d); 8.08 (2H, m); 8.24 (1H, t); 8.48 (1H, s); 10.01 (1H, s).

Workup

  1. temperaturethe mixture heated
  2. temperatureat gentle reflux for 2.75 hours
  3. temperatureto cool
  4. customThe solid which precipitated
  5. filtrationwas filtered
  6. washwashed with water and ether

Sources & evidence

ORD record
ord-d66ffe634d0f40d4b1b3bb395811f452
Source dataset
uspto-grants-2002_03
Patent number
US06362191B1

Reaction notes

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