Methanol → HCID 54046513, compound

HRID 2081744Notes

Reaction equation

HRID 2081744 reaction equation
CO.O1CCCC1.[CH:8](=[N:15][N:16]1[CH2:20][CH2:19][N:18]([C@@:21]2([C:48]([O:50][CH2:51][C:52]3[CH:57]=[CH:56][C:55]([N+:58]([O-:60])=[O:59])=[CH:54][CH:53]=3)=[O:49])[S:27][C@H:26]3[N:23]([C:24](=[O:47])[C:25]3([N:30]=CC3C=C(C(C)(C)C)C(O)=C(C(C)(C)C)C=3)[O:28][CH3:29])[CH2:22]2)[C:17]1=[O:61])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)([O-])O.[Na+]>[Cl-].N(C(=O)C[N+](C)(C)C)N.O.C(Cl)Cl>[NH2:30][C:25]1([O:28][CH3:29])[C:24](=[O:47])[N:23]2[C@@H:26]1[S:27][C@@:21]([N:18]1[CH2:19][CH2:20][N:16]([N:15]=[CH:8][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:17]1=[O:61])([C:48]([O:50][CH2:51][C:52]1[CH:57]=[CH:56][C:55]([N+:58]([O-:60])=[O:59])=[CH:54][CH:53]=1)=[O:49])[CH2:22]2

Participants

8

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 136067295HCID 136067295, compound

Product 1

HCID 54046513HCID 54046513, compoundYield 60.6%

Reagents, catalysts & solvents 3

HCID 67156Betaine Hydrazide HydrochlorideCatalystHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

In a mixed solvent consisting of 15 ml of methanol, 6 ml of tetrahydrofuran, 1.5 ml of water and 6 ml of methylene chloride was dissolved 740 mg of (3R,5R)-3-(3-benzylideneamino-2-oxoimidazolidin-1-yl)-6-(3,5-di-tert-butyl-4-hydroxybenzylideneamino)-6-methoxy-3-(p-nitrobenzyloxycarbonyl)-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane. Thereto was added 240 mg of a Girard reagent (2-hydrazino-N,N,N-trimethyl-2-oxoethanaminium chloride). The mixture was stirred at room temperature for 1 hour. To the reaction mixture were added 30 ml of methylene chloride and 10 ml of water. The resulting mixture was adjusted to pH 7.0 with a saturated aqueous sodium hydrogencarbonate solution. The organic layer was separated, washed with a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography (eluant: benzene/ethyl acetate=5/1 to 1/1) to obtain 320 mg (yield: 60.6%) of (3R,5R)-6-amino-3-(3-benzylideneamino-2-oxoimidazolidin-1-yl)-6-methoxy-3-(p-nitrobenzyloxycarbonyl)-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane.

Workup

  1. customThe organic layer was separated
  2. washwashed with a saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed by distillation under reduced pressure
  5. customThe residue was purified by column chromatography (eluant: benzene/ethyl acetate=5/1 to 1/1)

Sources & evidence

ORD record
ord-9ac1ab20ea4845ec8f0064181e065977
Source dataset
uspto-grants-1993_02
Patent number
US05185330

Reaction notes

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