Triethylamine → HCID 13430187, compound

HRID 2119224Notes

Reaction equation

HRID 2119224 reaction equation
[C:1]([O:4][C@@H:5]1[N:8]([CH:9]([C:14]([CH3:16])=[CH2:15])[C:10]([O:12][CH3:13])=[O:11])[C:7](=[O:17])[C@H:6]1[NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])(=[O:3])[CH3:2].C(N(CC)CC)C>C(Cl)Cl>[C:1]([O:4][C@@H:5]1[N:8]([C:9](=[C:14]([CH3:15])[CH3:16])[C:10]([O:12][CH3:13])=[O:11])[C:7](=[O:17])[C@H:6]1[NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 18609072HCID 18609072, compound

Product 1

HCID 13430187HCID 13430187, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.07 g (3 mmol) (2R) methyl 2-((3S,4S)-4-acetoxy-3-t-butyloxycarbonylaminoazetidine-2-on-1-yl)-3-methylbut-3-enoate in 30 ml of methylene chloride, at room temperature 0.3 ml of triethylamine is added and the reaction mixture stirred for 6 hours at room temperature. The reaction mixture is first washed with 15 ml of 1N hydrogen chloride in water and then with 15 ml of saturated sodium chloride solution. The organic layer is dried over sodium sulfate and the solvent removed in vacuo, leaving 1.07 g (100%) of a noncrystalline solid (title compound). IR spectrum in methylene chloride: 3420, 3000, 1790, 1760, 1725, 1505, 1385, 1365, 1215 and 1150 cm-1.

Workup

  1. washThe reaction mixture is first washed with 15 ml of 1N hydrogen chloride in water
  2. dry with materialThe organic layer is dried over sodium sulfate
  3. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-1c30a63af33b46be9113e683e905db30
Source dataset
uspto-grants-1987_07
Patent number
US04683303

Reaction notes

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