Dimethyl Sulfoxide → (2s,4r)-n-Tert-butoxycarbonyl-4-(n-tert-butoxycarbonylglycylamino)-2-pyrrolidinecarboxaldehyde

HRID 2185497Notes

Reaction equation

HRID 2185497 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[C:11]([O:15][C:16]([N:18]1[CH2:22][C@H:21]([NH:23][C:24](=[O:34])[CH2:25][NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:20][C@H:19]1[CH2:35][OH:36])=[O:17])([CH3:14])([CH3:13])[CH3:12].C(N(CC)CC)C>ClCCl>[C:11]([O:15][C:16]([N:18]1[CH2:22][C@H:21]([NH:23][C:24](=[O:34])[CH2:25][NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:20][C@H:19]1[CH:35]=[O:36])=[O:17])([CH3:13])([CH3:14])[CH3:12]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 70172939(2s,4r)-4-(n-Tert-butoxycarbonylglycylamino)-2-hydroxymethyl-n-tert-butoxycarbonylpyrrolidine

Product 1

HCID 73947491(2s,4r)-n-Tert-butoxycarbonyl-4-(n-tert-butoxycarbonylglycylamino)-2-pyrrolidinecarboxaldehydeYield 97.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The following reaction was carried under argon. Dimethyl sulfoxide (288 μL) was added to a stirred solution of oxalyl chloride (177 mL) in dichloromethane (3 mL) at −78° C. After stirring at the same temperature for 15 min, a solution of (2S,4R)-N-tert-butoxycarbonyl-4-(N-tert-butoxycarbonylglycylamino)-2-hydroxymethylpyrrolidine (151 mg) in dichloromethane (3 mL) was added. The mixture was stirred at −78° C. for 2 hr, and triethylamine (848 μL) was added to the reaction mixture. The mixture was stirred at 0° C. for 1 hr, quenched with saturated ammonium chloride, and extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate and evaporated in vacuo. The residue was purified by silica gel column chromatography (chloroform then chloroform:methanol=99:1 to 97:3, v/v) to give the titled compound (147 mg) as a colorless foam.

Workup

  1. customThe following reaction
  2. stirringThe mixture was stirred at −78° C. for 2 hr
  3. stirringThe mixture was stirred at 0° C. for 1 hr
  4. customquenched with saturated ammonium chloride
  5. extractionextracted with dichloromethane
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. customevaporated in vacuo
  8. customThe residue was purified by silica gel column chromatography (chloroform

Sources & evidence

ORD record
ord-03fc29335e094994a8fa838f145795ca
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

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