Trityl chloride → HCID 11123509, compound

HRID 975689Notes

Reaction equation

HRID 975689 reaction equation
C([S:4][C@@H:5]1[CH2:9][N:8]([C:10]([O:12][CH2:13][CH:14]=[CH2:15])=[O:11])[C@H:7]([CH2:16][C:17]#[N:18])[CH2:6]1)(=O)C.C[O-].[Na+].Cl[C:23]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(OCC)(=O)C>O1CCCC1.CO.O>[CH2:13]([O:12][C:10]([N:8]1[CH2:9][C@@H:5]([S:4][C:23]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)([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)[CH2:6][C@H:7]1[CH2:16][C:17]#[N:18])=[O:11])[CH:14]=[CH2:15]

Participants

8

Reactant 4

HCID 6456Trityl chlorideHCID 8857Ethyl AcetateHCID 10942334Sodium MethoxideHCID 54501361HCID 54501361, compound

Product 1

HCID 11123509HCID 11123509, compoundYield 83.8%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2R,4S)-4-acetylthio-1-allyloxycarbonyl-2-(cyanomethyl) pyrrolidine (8.20 g) in tetrahydrofuran (40 ml) and methanol (40 ml) was added a 28% sodium methoxide in methanol solution (6.03 ml) at ice-cooling. After stirring at ice-cooling for 30 minutes, chlorotriphenylmethane (8.31 g) was added to the cold solution. After stirring at the same temperature for 2 hours, the solution was poured into a mixture of ethyl acetate and water. The separated organic layer was washed with aqueous sodium chloride solution twice, dried over magnesium sulfate and evaporated. The residue was subjected to a column chromatography on silica gel (eluent; n-hexane:ethyl acetate=5:1) to give (2R,4S)-1-allyloxycarbonyl-2-cyanomethyl-4-(triphenylmethylthio)pyrrolidine (11.7 g).

Workup

  1. temperaturecooling
  2. temperaturecooling for 30 minutes
  3. stirringAfter stirring at the same temperature for 2 hours
  4. washThe separated organic layer was washed with aqueous sodium chloride solution twice
  5. dry with materialdried over magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-afcded8801fa4e6cb2688b157ec0cbc7
Source dataset
uspto-grants-1997_03
Patent number
US05608056

Reaction notes

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