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

HRID 1954051Notes

Reaction equation

HRID 1954051 reaction equation
O=[C:2]1NCN[C@@H](C([O-])=O)C1.[CH2:11]([O:18][C:19](=[O:44])[C@H:20]([NH:32][S:33]([C:36]1[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][CH:37]=1)(=[O:35])=[O:34])[CH2:21][C:22]([NH:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.O1COCOC1>ClCCl.S(=O)(=O)(O)O>[CH2:25]([N:24]1[C:22](=[O:23])[CH2:21][C@H:20]([C:19]([O:18][CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[O:44])[N:32]([S:33]([C:36]2[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][CH:37]=2)(=[O:35])=[O:34])[CH2:2]1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 3

HCID 80811,3,5-TrioxaneHCID 15896000HCID 15896000, compoundHCID 131722003HCID 131722003, compound

Product 1

HCID 15896001HCID 15896001, compound

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Benzyl 1-benzyl-3-1(4-methoxyphenyl)sulfonyl]-6oxo-hexahydro-pyrimidine-4(R)-carboxylate (1c): 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 (2x). The product is purified by flash silica gel chromatography (1:1 hexanes-ethyl acetate), to give benzyl 1-benyl-3-[(4-methoxyphenyl)sulfonyl]-6-oxo-hexahydro-pyrimidine4(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 (2x)
  5. customThe product is purified by flash silica gel chromatography (1:1 hexanes-ethyl acetate)

Sources & evidence

ORD record
ord-2bb97d9d98ed45759129ef29c25a9779
Source dataset
uspto-grants-2000_09
Patent number
US06121258

Reaction notes

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