Triethylamine → HCID 13124489, compound

HRID 2119226Notes

Reaction equation

HRID 2119226 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][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[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]([CH3:16])[CH3:15])[C:10]([O:12][CH3:13])=[O:11])[C:7](=[O:17])[C@H:6]1[NH:18][C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 18609071HCID 18609071, compound2×

Product 1

HCID 13124489HCID 13124489, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture containing 6.7 g (17.2 mmol) of (2R) methyl 2-((3S,4S)-4-acetoxy-3-benzyloxycarbonylaminoazetidine-2-on-1-yl)-3-methylbut-3-enoate and 1.8 ml of triethylamine in 180 ml of methylene chloride is refluxed for 60 minutes in a nitrogen atmosphere. After cooling of the solution it is washed subsequently with 100 ml aqueous 1N hydrogen chloride solution and 100 ml of saturated sodium chloride solution. The organic layer is dried over sodium sulfate, filtered and evaporated in vacuo. In this way, 6.6 g (98%) of title compound as a pure, noncrystalline solid is obtained. IR spectrum in methylene chloride: 3400, 3000, 1790, 1730, 1510 and 1210 cm-1.

Workup

  1. temperatureis refluxed for 60 minutes in a nitrogen atmosphere
  2. temperatureAfter cooling of the solution it
  3. washis washed subsequently with 100 ml aqueous 1N hydrogen chloride solution and 100 ml of saturated sodium chloride solution
  4. dry with materialThe organic layer is dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-607a6585f4434a56ad33237644db1a8b
Source dataset
uspto-grants-1987_07
Patent number
US04683303

Reaction notes

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