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

HRID 1649269Notes

Reaction equation

HRID 1649269 reaction equation
[CH:1]([O:14][C:15]([C:17]1[N:18]2[CH:21]([S:22](=[O:29])[CH2:23][C:24]=1[CH2:25][CH:26](Cl)[Cl:27])[CH:20]([NH:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C:19]2=[O:38])=[O:16])([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.C(N(CC)CC)C>O1CCCC1.C(OCC)(=O)C>[CH:1]([O:14][C:15]([C:17]1[N:18]2[CH:21]([S:22](=[O:29])[CH2:23][C:24]=1[CH:25]=[CH:26][Cl:27])[CH:20]([NH:30][C:31]([O:33][C:34]([CH3:36])([CH3:35])[CH3:37])=[O:32])[C:19]2=[O:38])=[O:16])([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 130787072-Benzhydryloxycarbonyl-7-t-butoxycarbonylamino-3-(2,2-dichloroethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-5-oxide2×

Product 1

HCID 537806992-Benzhydryloxycarbonyl-7-t-butoxycarbonylamino-3-(2-chlorovinyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-5-oxideYield 100.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-benzhydryloxycarbonyl-7-t-butoxycarbonylamino-3-(2,2-dichloroethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-5-oxide (product 11f) (3.3 g) and triethylamine (0.88 cc) in dry tetrahydrofuran (50 cc) is stirred at 25° C. for 16 hours and the reaction mixture is then diluted with ethyl acetate (200 cc). The organic solution is washed with distilled water (5×60 cc), dried over sodium sulphate and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 35° C. This yields a product (11e) (3.1 g) in the form of a hard orange foam.

Workup

  1. washThe organic solution is washed with distilled water (5×60 cc)
  2. dry with materialdried over sodium sulphate
  3. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 35° C

Sources & evidence

ORD record
ord-d79d2e8b96624d8f8f0b690305e7f37f
Source dataset
uspto-grants-1983_11
Patent number
US04415562

Reaction notes

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