1,3,5-Trioxane → HCID 15896001, compound

HRID 2184780Notes

Reaction equation

HRID 2184780 reaction equation
[CH2:1]([O:8][C:9](=[O:34])[C@H:10]([NH:22][S:23]([C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=1)(=[O:25])=[O:24])[CH2:11][C:12]([NH:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1COCO[CH2:36]1>ClCCl.S(=O)(=O)(O)O>[CH2:15]([N:14]1[C:12](=[O:13])[CH2:11][C@H:10]([C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:34])[N:22]([S:23]([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=2)(=[O:25])=[O:24])[CH2:36]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 80811,3,5-TrioxaneHCID 15896000HCID 15896000, compound

Product 1

HCID 15896001HCID 15896001, compound

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To the solution of N-benzyl-2(R)-[(4-methoxyphenyl)sulfonylamino]-succinamic acid benzyl ester as an oil (2.10 g, 4.4 mmol) in 200 mL of dichloromethane is added, with stirring, 1.3,5-trioxane (1.57 g, 17.4 mmol) followed by two drops of sulfuric acid. The reaction is heated at reflux for 3 hours at which time mass spectrometry (ES) indicates the reaction to be complete. The reaction is allowed to cool to room temperature, diluted with dichloromethane (250 mL), and washed with water (2×). The product is purified by flash silica gel chromatography (1:1 hexanes-ethyl acetate), to give benzyl 1-benzyl-3-[(4-methoxyphenyl)sulfonyl]-6-oxo-hexahydro-pyrimidine-4(R)-carboxylate.

Workup

  1. temperatureThe reaction is heated
  2. temperatureat reflux for 3 hours at which time mass spectrometry (ES)
  3. customthe reaction
  4. washwashed with water (2×)
  5. customThe product is purified by flash silica gel chromatography (1:1 hexanes-ethyl acetate)

Sources & evidence

ORD record
ord-53fca059b9ec4e76bc64c7fa86499f80
Source dataset
uspto-grants-2002_06
Patent number
US06399598B1

Reaction notes

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