Trityl chloride → HCID 57296959, compound

HRID 975699Notes

Reaction equation

HRID 975699 reaction equation
C([S:4][C@@H:5]1[CH2:9][N:8](OCC=C)[C@H:7]([CH2:14][CH2:15][N:16]=[N+:17]=[N-:18])[C:6]1=C=O)(=O)C.[CH3:21][O-].[Na+].[C:24]1([C:30](Cl)([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[C:44]([O:47][CH2:48][CH3:49])(=[O:46])C>CO.O>[CH2:48]([O:47][C:44]([N:8]1[CH2:9][C@@H:5]([S:4][C:30]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:6][C@H:7]1[CH2:14][CH2:15][N:16]=[N+:17]=[N-:18])=[O:46])[CH:49]=[CH2:21]

Participants

7

Reactant 4

HCID 6456Trityl chlorideHCID 8857Ethyl AcetateHCID 10942334Sodium MethoxideHCID 86750462HCID 86750462, compound

Product 1

HCID 57296959HCID 57296959, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (2R,4S)-4-acetylthio-1-allyloxy-carbonyl-2-(2-azidoethyl) pyrrolidine (14.7 g) in methanol (74 ml) was added dropwise 4.8N sodium methoxide in methanol (11.3 ml) under ice-cooling. After stirring for 1 hour at 0° C., triphenylmethyl chloride (14.4 g) was added to the mixture. After stirring for 5 hours at 0° C., the mixture was poured into ethyl acetate and water. The organic layer was separated and the aqueous layer was extracted twice with ethyl acetate. The combined organic layer was washed with water and brine, dried over magnesium sulfate, and evaporated under reduced pressure. The residue was column chromatographed on silica gel (hexane:ethyl acetate=10:1 to 5:1) to give (2R,4S)-1-allyloxycarbonyl-2-(2-azidoethyl)-4-(triphenylmethylthio)pyrrolidine (16.5 g).

Workup

  1. temperaturecooling
  2. stirringAfter stirring for 5 hours at 0° C.
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted twice with ethyl acetate
  5. washThe combined organic layer was washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated under reduced pressure
  8. customchromatographed on silica gel (hexane:ethyl acetate=10:1 to 5:1)

Sources & evidence

ORD record
ord-d761fac4cf9e48999d68d666c7d8a72b
Source dataset
uspto-grants-1997_03
Patent number
US05608056

Reaction notes

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