Triethylamine → HCID 11966734, compound

HRID 373329Notes

Reaction equation

HRID 373329 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, compoundYield 103.9%

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 (XVa, 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 0.245g of diphenylmethyl 2-[(3R,4R)-4-(p-toluenesulfonylthio)-3-phenoxyacetamido-2-oxo-azetidin-1-yl]-2,3-butadienoate (Ia) as a colorless foam (quantitative yield).

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-9f841bb85c574f638eb45e17d2b95e6b
Source dataset
uspto-grants-1992_11
Patent number
US05162524

Reaction notes

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