Triethyl phosphite → 432038-96-5

HRID 230047Notes

Reaction equation

HRID 230047 reaction equation
CC1(C)CC(=O)CC(=O)C1.C(=O)(O)[O-].[Na+].P(OCC)(OCC)OCC.[I-].[C:27]([CH2:30][N+:31]1[CH:36]=[CH:35][CH:34]=[C:33]([C:37]([C:39]2[N:40]=[CH:41][N:42]3[CH:46]=[C:45]([C:47]4[C@H:48]([CH3:64])[C@@H:49]5[C@@H:59]([C@H:60]([OH:62])[CH3:61])[C:58](=[O:63])[N:50]5[C:51]=4[C:52]([O:54]CC=C)=[O:53])[S:44][C:43]=23)=[O:38])[CH:32]=1)(=[O:29])[NH2:28]>O.O1CCCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:27]([CH2:30][N+:31]1[CH:36]=[CH:35][CH:34]=[C:33]([C:37]([C:39]2[N:40]=[CH:41][N:42]3[CH:46]=[C:45]([C:47]4[C@H:48]([CH3:64])[C@@H:49]5[C@@H:59]([C@H:60]([OH:62])[CH3:61])[C:58](=[O:63])[N:50]5[C:51]=4[C:52]([O-:54])=[O:53])[S:44][C:43]=23)=[O:38])[CH:32]=1)(=[O:29])[NH2:28]

Participants

8

Reactant 4

HCID 31215Triethyl phosphiteHCID 31358DimedoneHCID 516892Sodium BicarbonateHCID 131727434HCID 131727434, compound

Product 1

HCID 10300326432038-96-5Yield 71%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 0.28 g of dimedone, 0.13 g of sodium bicarbonate, and 0.06 ml of triethyl phosphite in 1 ml of water and 3 ml of tetrahydrofuran was stirred at room temperature for 10 min. The atmosphere was then replaced by argon, 22.4 mg of palladium acetate was added thereto, and the mixture was stirred for 10 min. 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 (0.66 g) was added thereto, and the mixture was stirred at 40° C. for 2 hr. The reaction mixture was stirred in an ice-water bath for 30 min, and the resultant precipitate was collected by filtration to give 0.47 g of a crude product 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 crude product was dissolved in 2 ml of water, and the solution was filtered through a filter with a pore diameter of 0.45 μm, followed by washing three times with 0.5 ml of water. The filtrate and the wash liquids were combined, and stirring was carried out at 4° C. for 12 hr. The resultant precipitate was collected by filtration to give 0.35 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.

Workup

  1. additionwas added
  2. stirringthe mixture was stirred at 40° C. for 2 hr
  3. stirringThe reaction mixture was stirred in an ice-water bath for 30 min
  4. filtrationthe resultant precipitate was collected by filtration
  5. customto give 0.47 g of a crude product 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
  6. filtrationthe solution was filtered through
  7. filtrationa filter with a pore diameter of 0.45 μm
  8. washby washing three times with 0.5 ml of water
  9. stirringstirring
  10. waitwas carried out at 4° C. for 12 hr
  11. filtrationThe resultant precipitate was collected by filtration

Sources & evidence

ORD record
ord-5ab672b338ff43b3bc390c7e5951abc2
Source dataset
uspto-grants-2009_07
Patent number
US07563901B2

Reaction notes

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