Triethylamine → 2-Benzhydryloxycarbonyl-7-t-butoxycarbonylamino-3-(2-nicotinoylaminothiazol-5-yl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene

HRID 1980426Notes

Reaction equation

HRID 1980426 reaction equation
Cl.[C:2](Cl)(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[N:5][CH:4]=1.[NH2:11][C:12]1[S:13][C:14]([C:17]2[CH2:24][S:23][CH:22]3[N:19]([C:20](=[O:33])[CH:21]3[NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C:18]=2[C:34]([O:36][CH:37]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[O:35])=[CH:15][N:16]=1.C(N(CC)CC)C.C(OCC)(=O)C>O1CCCC1>[CH:37]([O:36][C:34]([C:18]1[N:19]2[CH:22]([S:23][CH2:24][C:17]=1[C:14]1[S:13][C:12]([NH:11][C:2](=[O:9])[C:3]3[CH:8]=[CH:7][CH:6]=[N:5][CH:4]=3)=[N:16][CH:15]=1)[CH:21]([NH:25][C:26]([O:28][C:29]([CH3:31])([CH3:30])[CH3:32])=[O:27])[C:20]2=[O:33])=[O:35])([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:44]1[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 131759453-(2-Aminothiazol-5-yl)-2-benzhydryloxycarbonyl-7-t-butoxycarbonylamino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene

Product 1

HCID 204024552-Benzhydryloxycarbonyl-7-t-butoxycarbonylamino-3-(2-nicotinoylaminothiazol-5-yl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-eneYield 55.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
3 °C

Procedure

Nicotinoyl chloride hydrochloride (7.12 g) is added to a solution of 3-(2-aminothiazol-5-yl)-2-benzhydryloxycarbonyl-7-t-butoxycarbonylamino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene (11.3 g) in tetrahydrofuran (300 cc), cooled to 3° C., and triethylamine (11.12 cc) is then added in the course of 10 minutes. The mixture is stirred for 1 hour at 3° C. and then for 2 hours while allowing the temperature to ri$e to 20° C. The reaction mixture is poured into ethyl acetate (400 cc) and washed with distilled water (3×120 cc) and a saturated solution of sodium chloride (100 cc). The organic phase is dried and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The residue is crystallised from ethyl acetate (20 cc) to give 2-benzhydryloxycarbonyl-7-t-butoxycarbonylamino-3-(2-nicotinoylaminothiazol-5-yl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene (7.4 g) in the form of a yellow solid.

Workup

  1. waitfor 2 hours while allowing
  2. customto ri$e to 20° C
  3. washwashed with distilled water (3×120 cc)
  4. customThe organic phase is dried
  5. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C
  6. customThe residue is crystallised from ethyl acetate (20 cc)

Sources & evidence

ORD record
ord-96b5c765c1004d16bf9fcb9a7aeed991
Source dataset
uspto-grants-1985_04
Patent number
US04508717

Reaction notes

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