Pyridine → Methyl 2-ethoxy-3-{4-[2-(6-[(methoxyimino)(phenyl)methyl]-2-oxo-1,3-benzothiazol-3(2H)-yl)ethoxy]phenyl}propanoate

HRID 1790241Notes

Reaction equation

HRID 1790241 reaction equation
[C:1]([C:9]1[CH:36]=[CH:35][C:12]2[N:13]([CH2:17][CH2:18][O:19][C:20]3[CH:25]=[CH:24][C:23]([CH2:26][CH:27]([O:32][CH2:33][CH3:34])[C:28]([O:30][CH3:31])=[O:29])=[CH:22][CH:21]=3)[C:14](=[O:16])[S:15][C:11]=2[CH:10]=1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:38][O:39][NH2:40].N1C=CC=CC=1>CO>[CH2:33]([O:32][CH:27]([CH2:26][C:23]1[CH:24]=[CH:25][C:20]([O:19][CH2:18][CH2:17][N:13]2[C:12]3[CH:35]=[CH:36][C:9]([C:1](=[N:40][O:39][CH3:38])[C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[CH:10][C:11]=3[S:15][C:14]2=[O:16])=[CH:21][CH:22]=1)[C:28]([O:30][CH3:31])=[O:29])[CH3:34]

Participants

5

Reactant 3

HCID 1049PyridineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 11584254Methyl 3-{4-[2-(6-benzoyl-2-oxo-1,3-benzothiazol-3(2H)-yl)ethoxy]phenyl}-2-ethoxypropanoate

Product 1

HCID 72808510Methyl 2-ethoxy-3-{4-[2-(6-[(methoxyimino)(phenyl)methyl]-2-oxo-1,3-benzothiazol-3(2H)-yl)ethoxy]phenyl}propanoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 30 ml of methanol add the compound obtained in Step C (0.00198 mol), O-methyl-hydroxylamine hydrochloride (0.00594 mol) and pyridine (0.00594 mol). Heat at reflux for 3 hours. Evaporate to dryness. Add 100 ml of hydrochloric acid (1N) and then extract with 50 ml of dichloromethane twice. The organic phase is dried over MgSO4 and then evaporated to yield the title compound.

Workup

  1. temperatureHeat
  2. temperatureat reflux for 3 hours
  3. customEvaporate to dryness
  4. additionAdd 100 ml of hydrochloric acid (1N)
  5. extractionextract with 50 ml of dichloromethane twice
  6. dry with materialThe organic phase is dried over MgSO4
  7. customevaporated

Sources & evidence

ORD record
ord-e9e46de2e79a488992aeb4f0734723aa
Source dataset
uspto-grants-2006_07
Patent number
US07071221B2

Reaction notes

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