Nitrogen → HCID 9939995, compound

HRID 2289481Notes

Reaction equation

HRID 2289481 reaction equation
[Br-:1].[C:2]([C:5](=[CH2:53])[CH2:6][N+:7]1[CH:12]=[CH:11][C:10]([S:13][CH2:14][C:15]2[CH2:22][S:21][C@H:20]3[N:17]([C:18](=[O:36])[C@H:19]3[NH:23][C:24](=[O:35])[CH2:25][S:26][C:27]3[CH:32]=[C:31]([Cl:33])[CH:30]=[CH:29][C:28]=3[Cl:34])[C:16]=2[C:37]([O:39]C(C2C=CC=CC=2)C2C=CC=CC=2)=[O:38])=[CH:9][CH:8]=1)([OH:4])=[O:3].N#N.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>C(Cl)Cl>[Br-:1].[C:2]([C:5](=[CH2:53])[CH2:6][N+:7]1[CH:8]=[CH:9][C:10]([S:13][CH2:14][C:15]2[CH2:22][S:21][C@H:20]3[N:17]([C:18](=[O:36])[C@H:19]3[NH:23][C:24](=[O:35])[CH2:25][S:26][C:27]3[CH:32]=[C:31]([Cl:33])[CH:30]=[CH:29][C:28]=3[Cl:34])[C:16]=2[C:37]([OH:39])=[O:38])=[CH:11][CH:12]=1)([OH:4])=[O:3]

Participants

6

Reactant 4

HCID 947NitrogenHCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 15478821HCID 15478821, compound

Product 1

HCID 9939995HCID 9939995, compoundYield 68.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A slurry of 1-[2-carboxy-2-propen-1-yl]-4-[[(6R)-trans-2-(diphenylmethyl carboxy)-8-oxo-7-[(2,5-dichlorophenylthio)acetamido]-5-thia-1-azabicyclo[4.2.0]-oct-2-en-3-yl]methylthio]pyridinium bromide (580 mg, 0.665 mmol) in 22 mL of CH2Cl2 was cooled to 0° C. (ice bath) under an atomosphere of N2. Anisole (2.8 mL) was added followed by trifluoroacetic acid (8 mL). The cooling bath was removed, and the reaction was allowed to stir at rt for 1 h. The solution was concentrated in vacuo to remove the CH2Cl2 and most of the trifluoroacetic acid. The residue was treated with ether to precipitate a yellow solid. This solid was collected by filtration washing with ether. The solid was stirred with ethyl acetate for 30 min. stirred with acetone for 30 min., collected by filtration, and dried in vacuo to give 322 mg (66%) of 1-[2-carboxy-2-propen-1-yl]-4-[[(6R)-trans-2-carboxy-8-oxo-7-[(2,5-dichlorophenylthio)acetamido]-5-thia-1-azabicyclo[4.2.0]-oct-2-en-3-yl]methylthio]pyridinium bromide as a tan solid. 1H NMR (DMSO-d6) δ9.27 (d, J=8 Hz, 1H), 8.73 (d, J=6 Hz, 2H), 8.06 (d, J=6 Hz, 2H), 7.45-8.48 (m, 2H), 7.24 (dd, J=2,9 Hz, 2H), 6.41 (s, 1H), 6.08 (s, 1H), 5.63 (dd, J=5,8 Hz, 1H), 5.19 (s, 2H), 5.09 (d, J=5 Hz, 1H), 4.43 (s, 2H), 3.92 (s, 2H), 3.70 (d, J=18 Hz, 1H), 3.48 (d, J=18 Hz, 1H). IR (KBr) 1774, 1702, 1680, 1628, 1106 cm-1 ; MS (ESI) 626 (MH)+, Anal: Calcd for C25H21N3O6S3Cl2 ×HBr×0.5Me2CO; C, 42.44; H, 3.13; N, 5.94. Found: C, 43.25; H, 3.42, N, 5.71.

Workup

  1. customThe cooling bath was removed
  2. concentrationThe solution was concentrated in vacuo
  3. customto remove the CH2Cl2
  4. additionThe residue was treated with ether
  5. customto precipitate a yellow solid
  6. filtrationThis solid was collected by filtration
  7. washwashing with ether
  8. stirringThe solid was stirred with ethyl acetate for 30 min.
  9. stirringstirred with acetone for 30 min.
  10. filtrationcollected by filtration
  11. customdried in vacuo

Sources & evidence

ORD record
ord-3086cda89fde4e829a97c7251b40646d
Source dataset
uspto-grants-2000_07
Patent number
US06093712

Reaction notes

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