HCID 67330927, compound → Ethyl 2,7-dimethyl-6-{[(3R)-1-{[(2-methyl-2-propanyl)oxy]carbonyl}-3-piperidinyl](2-propanyl)carbamoyl}-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate

HRID 244377Notes

Reaction equation

HRID 244377 reaction equation
[CH3:1][C:2]([O:13][C:14]1[CH:19]=[C:18]([CH3:20])[C:17]([C:21](=[O:39])[N:22]([C@@H:26]2[CH2:31][CH2:30][CH2:29][N:28]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:27]2)[CH:23]([CH3:25])[CH3:24])=[CH:16][C:15]=1[N+:40]([O-])=O)([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:3](OCC)=[O:4]>C(O)(=O)C.[Fe]>[CH3:1][C:2]1([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:3](=[O:4])[NH:40][C:15]2[CH:16]=[C:17]([C:21](=[O:39])[N:22]([C@@H:26]3[CH2:31][CH2:30][CH2:29][N:28]([C:32]([O:34][C:35]([CH3:37])([CH3:38])[CH3:36])=[O:33])[CH2:27]3)[CH:23]([CH3:24])[CH3:25])[C:18]([CH3:20])=[CH:19][C:14]=2[O:13]1

Participants

4

Reactant 1

HCID 67330927HCID 67330927, compound

Product 1

HCID 67512567Ethyl 2,7-dimethyl-6-{[(3R)-1-{[(2-methyl-2-propanyl)oxy]carbonyl}-3-piperidinyl](2-propanyl)carbamoyl}-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylateYield 57.1%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent2×

Procedure

Subsequently, to a suspension of iron (110 g) in acetic acid (500 ml) was added dropwise a solution of the obtained diethyl methyl(5-methyl-4-{[(3R)-1-{[(2-methyl-2-propanyl)oxy]carbonyl}-3-piperidinyl](2-propanyl)carbamoyl}-2-nitrophenoxy)propanedioate (205 g) in acetic acid (200 ml) slowly at 90° C. Ten hours later, the mixture was allowed to cool to room temperature, filtered through celite, and the filtrate was concentrated under reduced pressure. To the obtained residue was added a saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with chloroform. The organic layer was washed with water and a saturated aqueous sodium chloride solution, dried over sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel chromatography to give the title compound (102 g).

Workup

  1. customTen hours
  2. filtrationfiltered through celite
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionTo the obtained residue was added a saturated aqueous sodium hydrogen carbonate solution
  5. extractionthe mixture was extracted with chloroform
  6. washThe organic layer was washed with water
  7. dry with materiala saturated aqueous sodium chloride solution, dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated under reduced pressure
  10. customthe resulting residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-0d6ab138496a43aeb6fe208212c1ec9c
Source dataset
uspto-grants-2014_02
Patent number
US08658639B2

Reaction notes

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