N-Methylaniline → 432038-96-5

HRID 230048Notes

Reaction equation

HRID 230048 reaction equation
C(=O)(O)[O-].[Na+].CNC1C=CC=CC=1.P(OCC)(OCC)OCC.[I-].[C:25]([CH2:28][N+:29]1[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([C:37]2[N:38]=[CH:39][N:40]3[CH:44]=[C:43]([C:45]4[C@H:46]([CH3:62])[C@@H:47]5[C@@H:57]([C@H:58]([OH:60])[CH3:59])[C:56](=[O:61])[N:48]5[C:49]=4[C:50]([O:52]CC=C)=[O:51])[S:42][C:41]=23)=[O:36])[CH:30]=1)(=[O:27])[NH2:26]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CC(O)C.O>[C:25]([CH2:28][N+:29]1[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([C:37]2[N:38]=[CH:39][N:40]3[CH:44]=[C:43]([C:45]4[C@H:46]([CH3:62])[C@@H:47]5[C@@H:57]([C@H:58]([OH:60])[CH3:59])[C:56](=[O:61])[N:48]5[C:49]=4[C:50]([O-:52])=[O:51])[S:42][C:41]=23)=[O:36])[CH:30]=1)(=[O:27])[NH2:26]

Participants

8

Reactant 4

HCID 7515N-MethylanilineHCID 31215Triethyl phosphiteHCID 516892Sodium BicarbonateHCID 131727434HCID 131727434, compound

Product 1

HCID 10300326432038-96-5Yield 16.2%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent2×HCID 3776IsopropanolSolvent3×

Procedure

Sodium bicarbonate (6.72 g), 10.4 ml of N-methylaniline, and 4.8 ml of triethyl phosphite were added in that order to 320 ml of a mixed liquid of 2-propanol:water=3:2. The atmosphere was replaced by argon, and the mixture was stirred at room temperature for 15 min. Palladium acetate (0.90 g) was then added thereto, and the mixture was stirred for 10 min. A solution of 59.31 g of allyl(1S,5R,6S)-2-[7-(1-carbamoylmethylpyridinium-3-yl)carbonylimidazo[5,1-b]thiazol-2-yl]-6-[(1R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylate iodide in 400 ml of a mixed liquid of 2-propanol:water=3:2 was added to the reaction mixture, and the mixture was stirred at 30° C. for one hr. 2-Propanol (80 ml) was added to the reaction mixture, and the mixture was stirred in an ice-water bath for one hr. The resultant precipitate was then collected by filtration and was washed with 265 ml of a cooled mixed liquid of 2-propanol:water=2:1, 53 ml of 2-propanol, and 106 ml of acetone in that order to give 7.168 g of (1S,5R,6S)-2-[7-(1-carbamoylmethylpyridinium-3-yl)carbonylimidazo[5,1-b]thiazol-2-yl]-6-[(1R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylate. This product was analyzed by NMR. The results were in agreement with the results of analysis in Example A-2.

Workup

  1. stirringthe mixture was stirred for 10 min
  2. stirringthe mixture was stirred at 30° C. for one hr
  3. stirringthe mixture was stirred in an ice-water bath for one hr
  4. filtrationThe resultant precipitate was then collected by filtration
  5. washwas washed with 265 ml of a cooled
  6. additionmixed liquid of 2-propanol

Sources & evidence

ORD record
ord-7a1a1cb08d6b46b4abc271207629cd7a
Source dataset
uspto-grants-2009_07
Patent number
US07563901B2

Reaction notes

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