Dimethylformamide → (2R,4S)-1-(p-nitrobenzyloxycarbonyl)-2-methoxycarbonylmethyl-4-acetylthiopyrrolidine

HRID 1088262Notes

Reaction equation

HRID 1088262 reaction equation
[N+:1]([C:4]1[CH:26]=[CH:25][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:16][C@@H:15]([S:17][C:18](=[O:20])[CH3:19])[CH2:14][C@H:13]2[CH2:21][C:22]([OH:24])=[O:23])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:27](Cl)(=O)C(Cl)=O.CN(C)C=O>C(Cl)Cl>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:16][C@@H:15]([S:17][C:18](=[O:20])[CH3:19])[CH2:14][C@H:13]2[CH2:21][C:22]([O:24][CH3:27])=[O:23])=[O:11])=[CH:25][CH:26]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 14830201(2R,4S)-1-(p-Nitrobenzyloxycarbonyl)-2-carboxymethyl-4-acetylthiopyrrolidine

Product 1

HCID 15671457(2R,4S)-1-(p-nitrobenzyloxycarbonyl)-2-methoxycarbonylmethyl-4-acetylthiopyrrolidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2R,4S)-1-(p-Nitrobenzyloxycarbonyl)-2-carboxymethyl-4-acetylthiopyrrolidine (148 mg) was dissolved in 2 ml of dry methylene chloride, and 0.2 ml of oxalyl chloride and a catalytic amount of dimethylformamide were added thereto, followed by stirring at room temperature for 2 hours. The reaction mixture was distilled to remove the solvent, and dry benzene was added thereto, followed by distillation of benzene. After two times repetition of the above procedure, the residue was dissolved in 2 ml of dry methylene chloride. The solution was added to a mixture of methanol (125 mg), triethylamine (81 mg) and dry methylene chloride (1 ml) under nitrogen stream with ice-cooling and stirred at the same temperature for 2 hours. The reaction mixture was washed successively with water and dilute hydrochloric acid, dried over anhydrous sodium sulfate and distilled to remove the solvent to obtain (2R,4S)-1-(p-nitrobenzyloxycarbonyl)-2-methoxycarbonylmethyl-4-acetylthiopyrrolidine.

Workup

  1. distillationThe reaction mixture was distilled
  2. customto remove the solvent, and dry benzene
  3. additionwas added
  4. distillationfollowed by distillation of benzene
  5. dissolutionAfter two times repetition of the above procedure, the residue was dissolved in 2 ml of dry methylene chloride
  6. additionThe solution was added to a mixture of methanol (125 mg), triethylamine (81 mg) and dry methylene chloride (1 ml) under nitrogen stream with ice-
  7. temperaturecooling
  8. stirringstirred at the same temperature for 2 hours
  9. washThe reaction mixture was washed successively with water and dilute hydrochloric acid
  10. dry with materialdried over anhydrous sodium sulfate
  11. distillationdistilled
  12. customto remove the solvent

Sources & evidence

ORD record
ord-7e6fee572cae4339a5fda28929944b57
Source dataset
uspto-grants-1990_10
Patent number
US04962103

Reaction notes

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