Water → HCID 70029515, compound

HRID 1370684Notes

Reaction equation

HRID 1370684 reaction equation
C[Si](OC([CH:8]1[S:15][C@H:14]2[N:11]([C:12](=[O:21])[C@H:13]2[NH:16][Si](C)(C)C)[CH:10]=[C:9]1/[CH:22]=[CH:23]/[CH2:24][I:25])=O)(C)C.[CH2:26]1[N:31]2[CH2:32][CH2:33][N:28]([CH2:29][CH2:30]2)[CH2:27]1.C[CH:35]([OH:37])C.[OH2:38]>ClCCl.C(#N)C>[IH:25].[IH:25].[NH2:16][C@@H:13]1[C:12](=[O:21])[N:11]2[C@@H:14]1[S:15][CH2:8][C:9](/[CH:22]=[CH:23]/[CH2:24][N+:28]13[CH2:33][CH2:32][N:31]([CH2:30][CH2:29]1)[CH2:26][CH2:27]3)=[C:10]2[C:35]([OH:37])=[O:38]

Participants

7

Reactant 4

HCID 962WaterHCID 3776IsopropanolHCID 9237DabcoHCID 70029530HCID 70029530, compound

Product 1

HCID 70029515HCID 70029515, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 30.6 g (0.06 mol) of (E)-(6R,7R)-3-(3-iodo-propenyl)-8-oxo-7-trimethylsilanylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-4-carboxylic acid trimethylsilanyl ester in 0.22 l of dichloromethane was added at 0° over 5 min a solution of 16.8 g (0.15 mol) of 1,4-diazobicyclo[2.2.2]octane in 0.15 l of acetonitrile. The dark reaction mixture was stirred at 0° for 4 h and then, 0.15 l of 2-propanol were added over 3 min, a precipitate being formed. After stirring was continued for 0.5 h, the pecipitated material was filtered off, washed with 0.1 l of 2-propanol and dried. For purification, this material was dissolved in 0.5 l of water and the pH of the solution was adjusted to 2.5 by the addition of 47% aqueous hydroiodic acid. After stirring for 15 min at 20°, a brown precipitate was filtered off and the clear solution was concentrated in vacuo to a volume of 0.25 l. Upon addition of 1.8 l of 2-propanol a precipitate formed which was isolated by filtration. The crude product was dissolved again in 0.41 of water, and, after removing insoluble material and concentration of the solution to a volume of 0.25 l, the product was precipitated by the addition of 1.5 l of 2-propanol to give 20.4 g of (E)-(6R,7R)-7-amino-3-[3-(4-aza-1-azonia-bicyclo[2,2,2]octan-1-yl)-propenyl]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid dihydroiodide as a pale-yellow solid.

Workup

  1. customThe dark reaction mixture
  2. customa precipitate being formed
  3. stirringAfter stirring
  4. waitwas continued for 0.5 h
  5. filtrationthe pecipitated material was filtered off
  6. washwashed with 0.1 l of 2-propanol
  7. customdried
  8. customFor purification
  9. dissolutionthis material was dissolved in 0.5 l of water
  10. additionthe pH of the solution was adjusted to 2.5 by the addition of 47% aqueous hydroiodic acid
  11. stirringAfter stirring for 15 min at 20°
  12. filtrationa brown precipitate was filtered off
  13. concentrationthe clear solution was concentrated in vacuo to a volume of 0.25 l
  14. additionUpon addition of 1.8 l of 2-propanol a precipitate
  15. customformed which
  16. customwas isolated by filtration
  17. customafter removing insoluble material and concentration of the solution to a volume of 0.25 l
  18. customthe product was precipitated by the addition of 1.5 l of 2-propanol

Sources & evidence

ORD record
ord-2055bc2a8a3e497c91cf19e39ea2feb9
Source dataset
uspto-grants-2003_06
Patent number
US06583133B1

Reaction notes

Loading…