Hydrochloric Acid → HCID 53653767, compound

HRID 1376830Notes

Reaction equation

HRID 1376830 reaction equation
[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=[N:53][O:54][CH3:55])[C:27]([NH:29][CH:30]2[CH:33]([CH2:34][S:35][C:36](=[C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][NH:47]3)[C:37](=[O:45])[C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[NH:32][C:31]2=[O:52])=[O:28])[N:25]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1N2CCN(CC2)C1.Cl>C(Cl)Cl.CCOCC>[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=[N:53][O:54][CH3:55])[C:27]([NH:29][CH:30]2[C:31](=[O:52])[N:32]3[CH:33]2[CH2:34][S:35][CH:36]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][N:47]=2)[C:37]3([OH:45])[C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])=[O:28])[N:25]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 9237DabcoHCID 178502779HCID 178502779, compound

Product 1

HCID 53653767HCID 53653767, compoundYield 61.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

3.053 g of the product of Step B and 1.3 g of triethylene diamine were dissolved in 30 ml of methylene chloride and the mixture was stirred for 1 hour and 30 minutes. Then 28 ml of N hydrochloric acid were added and extraction was effected with methylene chloride. The organic phase was dried and concentrated to dryness under reduced pressure. The residue was chromatographed on silica and eluted with a mixture of methylene chloride and ethyl acetate. The fraction rich in the expected product were recovered, the solvents were expelled and the crystals formed were taken up in ether to obtain 1.885 g of 1,1-dimethylethyl 7-[2-(2-tritylaminothiazol-4-yl)-2-methoxyimino-acetamido]-8-oxo-2-hydroxy-3-(2-pyridyl)-4-thia-1-azabicyclo[4,2,0]octane-2-carboxylate.

Workup

  1. extractionextraction
  2. customThe organic phase was dried
  3. concentrationconcentrated to dryness under reduced pressure
  4. customThe residue was chromatographed on silica
  5. washeluted with a mixture of methylene chloride and ethyl acetate
  6. customThe fraction rich in the expected product were recovered
  7. customthe crystals formed

Sources & evidence

ORD record
ord-72e1d490ed0a46e6903bf83171c81f52
Source dataset
uspto-grants-1997_09
Patent number
US05663164

Reaction notes

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