Ethyl Acetate → HCID 53635031, compound

HRID 975694Notes

Reaction equation

HRID 975694 reaction equation
C[O-].[Na+].Cl.[CH2:5]([O:8][C:9]([N:11]1[CH2:15][C@@H:14]([S:16][C:17]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:13][C@H:12]1[CH2:36][C:37](=[NH:39])[NH2:38])=[O:10])[CH:6]=[CH2:7].CN(C)[CH:42]=[CH:43][CH:44]=O.C(OCC)(=O)C>CO.O>[CH2:5]([O:8][C:9]([N:11]1[CH2:15][C@@H:14]([S:16][C:17]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:13][C@H:12]1[CH2:36][C:37]1[N:38]=[CH:44][CH:43]=[CH:42][N:39]=1)=[O:10])[CH:6]=[CH2:7]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 791253-(Dimethylamino)-2-propenalHCID 10942334Sodium MethoxideHCID 67705500HCID 67705500, compound

Product 1

HCID 53635031HCID 53635031, compoundYield 7.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

To a solution of 28% sodium methoxide in methanol solution (104 mg) in methanol (10 ml) were added (2R,4S)-1-allyloxycarbonyl-2-amidinomethyl-4-(triphenylmethylthio)pyrrolidine hydrochloride (1.0 g) and 3-dimethylaminoacrylaldehyde (190 mg). After stirring under reflux for 8 hours, the solution was poured into a mixture of ethyl acetate and water. The separated organic layer was washed with aqueous sodium chloride solution, dried over magnesium sulfate and evaporated. The residue was subjected to column chromatography on silica gel to give (2R,4S)-1-allyloxycarbonyl-2-(pyrimidin-2-ylmethyl)-4-(triphenylmethylthio) pyrrolidine (75 mg).

Workup

  1. temperatureunder reflux for 8 hours
  2. washThe separated organic layer was washed with aqueous sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-9f572e30b0fc495baf4cff86a1a37f2f
Source dataset
uspto-grants-1997_03
Patent number
US05608056

Reaction notes

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