Hydrochloric Acid → HCID 131712371, compound

HRID 1758713Notes

Reaction equation

HRID 1758713 reaction equation
[CH3:1][C:2]1[CH2:3][S:4][C@@H:5]2[CH:12]([NH:13][C:14](=[O:43])[C:15]([C:18]3[N:19]=[C:20]([NH:23][C:24]([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[S:21][CH:22]=3)=[N:16][OH:17])[C:11](=[O:44])[N:6]2[C:7]=1[C:8]([OH:10])=[O:9].C(Cl)Cl.Br[CH2:49][C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51].Cl>O>[CH3:1][C:2]1[CH2:3][S:4][C@@H:5]2[CH:12]([NH:13][C:14](=[O:43])[C:15]([C:18]3[N:19]=[C:20]([NH:23][C:24]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)([C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=4)[C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[S:21][CH:22]=3)=[N:16][O:17][CH2:49][C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])[C:11](=[O:44])[N:6]2[C:7]=1[C:8]([OH:10])=[O:9].[CH2:5]([NH:6][CH2:7][CH3:2])[CH3:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 79177tert-Butyl bromoacetateHCID 131712368HCID 131712368, compound

Product 1

HCID 131712371HCID 131712371, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4.7 g of the product of Step B were added to 70 ml of methylene chloride and then 70 ml of distilled water were added thereto. 21 ml of trithylamine were added thereto with stirring and under reduced pressure and after 5 minutes of stirring, 15.3 ml of tert.-butyl bromoacetate were added thereto all at once. The mixture was vigorously stirred at 25°-30° C. for 30 minutes and was then acidified at 15°-20° C. by addition of 8 ml of hydrochloric acid. The decanted aqueous phase was extracted twice with 20 ml of methylene chloride and the combined organic phases were washed 3 times with 50 ml of distilled water, was dried over magnesium sulfate and was vacuum filtered. The filtrate was rinsed and the filtrate was evaporated to dryness under reduced pressure. The 9.8 g of gum were dissolved in 30 ml of ethyl acetate and the mixture was stirred at 20° C. until dissolution occured. 0.75 ml of diethylamine were added thereto followed by the addition of 60 ml of isopropyl ether and the mixture was stirred at 20°-25° C. for 15 minutes and was then vacuum filtered. The recovered product was washed twice with 5 ml of a 1-2 ethyl acetate-isopropyl ether mixture and 3 times with 10 ml of isopropyl ether and was dried to obtain 4.31 g of the syn isomer of diethylamine 3-methyl-7-[2-(2-tritylamino-4-thiazolyl)-2-(tert.-butoxycarbonylmethoxyimino)-acetamido]-ceph-3-eme-4-carboxylate melting at 140° C. (decomposition).

Workup

  1. addition21 ml of trithylamine were added
  2. stirringof stirring
  3. stirringThe mixture was vigorously stirred at 25°-30° C. for 30 minutes
  4. extractionThe decanted aqueous phase was extracted twice with 20 ml of methylene chloride
  5. washthe combined organic phases were washed 3 times with 50 ml of distilled water
  6. dry with materialwas dried over magnesium sulfate
  7. filtrationfiltered
  8. washThe filtrate was rinsed
  9. customthe filtrate was evaporated to dryness under reduced pressure
  10. dissolutionThe 9.8 g of gum were dissolved in 30 ml of ethyl acetate
  11. stirringthe mixture was stirred at 20° C. until dissolution
  12. addition0.75 ml of diethylamine were added
  13. additionthereto followed by the addition of 60 ml of isopropyl ether
  14. stirringthe mixture was stirred at 20°-25° C. for 15 minutes
  15. filtrationvacuum filtered
  16. washThe recovered product was washed twice with 5 ml of a 1-2 ethyl acetate-isopropyl ether mixture and 3 times with 10 ml of isopropyl ether
  17. customwas dried

Sources & evidence

ORD record
ord-e8975f6b073548559a035635933a1c3b
Source dataset
uspto-grants-1983_02
Patent number
US04374834

Reaction notes

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