Triethylamine → HCID 11966734, compound

HRID 373346Notes

Reaction equation

HRID 373346 reaction equation
[C:1]1([CH3:54])[CH:6]=[CH:5][C:4]([S:7]([S:10][C@H:11]2[N:14]([C:15](=[C:32](OS(C(F)(F)F)(=O)=O)[CH3:33])[C:16]([O:18][CH:19]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:17])[C:13](=[O:42])[C@H:12]2[NH:43][C:44](=[O:53])[CH2:45][O:46][C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)(=[O:9])=[O:8])=[CH:3][CH:2]=1.C(N(CC)CC)C>O1CCCC1>[C:1]1([CH3:54])[CH:6]=[CH:5][C:4]([S:7]([S:10][C@H:11]2[N:14]([C:15](=[C:32]=[CH2:33])[C:16]([O:18][CH:19]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:17])[C:13](=[O:42])[C@H:12]2[NH:43][C:44](=[O:53])[CH2:45][O:46][C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)(=[O:8])=[O:9])=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 53766249HCID 53766249, compound

Product 1

HCID 11966734HCID 11966734, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Embodiment a: A solution of diphenylmethyl 2-[(3R,4R)-4-(p-toluenesulfonylthio)-3-phenoxyacetamido-2-oxo-azetidin-1-yl]-3-trifluoromethanesulfonyloxy-2-butenoate (XXa, 0.300 g, 0.00036 mole) in dry tetrahydrofuran (3 mL) was treated with triethylamine (0.077 mL, 0.00036 mole) for 1 h at room temperature. Reverse-phase chromatography (C-18 column, eluting with 65% acetonitrile--35% of 0.01M phosphate pH 6.5 buffer) showed complete consumption of the starting material after 45 min with formation of a single, faster-eluting product. 0.05M sulfuric acid and ethyl acetate was added to the reaction mixture, followed by separating the two phases. The organic phase was dried with sodium sulfate and evaporated to give diphenylmethyl 2-[(3R,4R)-4-(p-toluenesulfonylthio)-3-phenoxyacetamido-2-oxo-azetidin-1-yl]-2,3-butadienoate (Ia) as a colorless foam (0.245 g, quantitative).

Workup

  1. washReverse-phase chromatography (C-18 column, eluting with 65% acetonitrile--35% of 0.01M phosphate pH 6.5 buffer)
  2. customconsumption of the starting material after 45 min with formation of a single,
  3. washfaster-eluting product
  4. addition0.05M sulfuric acid and ethyl acetate was added to the reaction mixture
  5. customby separating the two phases
  6. dry with materialThe organic phase was dried with sodium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-d37f8a4716a8433e88a532ea5dd9b426
Source dataset
uspto-grants-1992_11
Patent number
US05162521

Reaction notes

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