Triethylamine → HCID 53870471, compound

HRID 258432Notes

Reaction equation

HRID 258432 reaction equation
[C:1]1([CH3:48])[CH:6]=[CH:5][C:4]([S:7]([S:10][C@H:11]2[N:14]([C:15](=[C:29](OS(C)(=O)=O)[CH3:30])[C:16]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=3)=[O:17])[C:13](=[O:36])[C@H:12]2[NH:37][C:38](=[O:47])[CH2:39][O:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)(=[O:9])=[O:8])=[CH:3][CH:2]=1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[C:1]1([CH3:48])[CH:6]=[CH:5][C:4]([S:7]([S:10][C@H:11]2[N:14]([C:15](=[C:29]=[CH2:30])[C:16]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=3)=[O:17])[C:13](=[O:36])[C@H:12]2[NH:37][C:38](=[O:47])[CH2:39][O:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)(=[O:8])=[O:9])=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 54277373HCID 54277373, compound

Product 1

HCID 53870471HCID 53870471, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 4-nitrobenzyl 2-[(3R,4R)-4-(p-toluenesulfonylthio)-3-phenoxyacetamido-2-oxo-azetidin-1-yl]-3-methanesulfonyloxy-2-butenoate (XVc, 0.0714 g, 0.00010 mole) in chloroform (1 mL) was treated with triethylamine (0.014 mL, 0.00010 mole) at room temperature. After a period of 1 h, reverse-phase C-18 HPLC indicated consumption of the starting material with formation of a single new peak (eluting phase: 65% acetonitrile and 35% 0.01M phosphate pH 6.5 buffer). Dilute hydrochloric acid (chilled at 0° C.) and ethyl acetate were added. The organic layer was washed with cold water, dried (sodium sulfate) and concentrated to give 0.0615 g (ca. 100%) of the title compound as a foam. The product was characterized by its 1H-NMR spectrum.

Workup

  1. customconsumption of the starting material
  2. washwith formation of a single new peak (eluting phase: 65% acetonitrile and 35% 0.01M phosphate pH 6.5 buffer)
  3. additionDilute hydrochloric acid (chilled at 0° C.) and ethyl acetate were added
  4. washThe organic layer was washed with cold water
  5. dry with materialdried (sodium sulfate)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-71668cbab9444987afc2dde988ffae15
Source dataset
uspto-grants-1993_11
Patent number
US05266691

Reaction notes

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