HCID 21962571, compound → HCID 21962582, compound

HRID 2211812Notes

Reaction equation

HRID 2211812 reaction equation
C(OC([N:11]([CH2:19][CH2:20][CH2:21][N:22]1[C:27]2[CH:28]=[CH:29][C:30]([C:32]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)([CH3:39])[CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])=[CH:31][C:26]=2[O:25][CH2:24][C:23]1=[O:46])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N+:13]=1[O-])=O)C1C=CC=CC=1>O1CCCC1.[Ti](Cl)(Cl)(Cl)Cl>[N:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[NH:11][CH2:19][CH2:20][CH2:21][N:22]1[C:27]2[CH:28]=[CH:29][C:30]([C:32]([C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=3)([CH3:39])[CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])=[CH:31][C:26]=2[O:25][CH2:24][C:23]1=[O:46]

Participants

4

Reactant 1

HCID 21962571HCID 21962571, compound

Product 1

HCID 21962582HCID 21962582, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of titanium (IV) chloride in tetrahydrofuran under nitrogen atmosphere, is added an equimolar amount of stannous chloride dihydrate, and the mixture is stirred 1 hour at room temperature. Then, a solution of ethyl 3-[(4-{3-[N-benzyloxycarbonyl-N-(1-oxido-2-pyridinyl)amino]propyl}-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl)]-3-phenylbutanoate is added and the mixture heated 3 hours at 40° C. After evaporation of the solvent, ice and aqueous sodium bicarbonate are added, the mixture extracted with ethyl acetate, and the organic layers are combined and dried over sodium sulfate. The solvent is evaporated, the residue is dissolved in ethanol, 10% Pd/C is added and the compound hydrogenated in a Parr apparatus. The solvent is then evaporated and the product is isolated by column chromatography.

Workup

  1. temperaturethe mixture heated 3 hours at 40° C
  2. customAfter evaporation of the solvent, ice and aqueous sodium bicarbonate
  3. additionare added
  4. extractionthe mixture extracted with ethyl acetate
  5. dry with materialdried over sodium sulfate
  6. customThe solvent is evaporated
  7. dissolutionthe residue is dissolved in ethanol
  8. addition10% Pd/C is added
  9. customThe solvent is then evaporated
  10. customthe product is isolated by column chromatography

Sources & evidence

ORD record
ord-c84b622b2633457c8647fc22e38684f7
Source dataset
uspto-grants-2006_09
Patent number
US07101876B2

Reaction notes

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