Hydrochloric Acid → HCID 57191012, compound

HRID 2289052Notes

Reaction equation

HRID 2289052 reaction equation
CS(C)=O.[OH:5][CH2:6][C@@H:7]1[CH2:11][C@H:10]([S:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH2:9][N:8]1[C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=1)=[O:23].C(N(CC)CC)C.Cl>C(Cl)Cl.C(Cl)(=O)C(Cl)=O>[CH:6]([C@@H:7]1[CH2:11][C@H:10]([S:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH2:9][N:8]1[C:22]([O:24][CH2:25][C:26]1[CH:27]=[CH:28][C:29]([N+:32]([O-:34])=[O:33])=[CH:30][CH:31]=1)=[O:23])=[O:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 57200321HCID 57200321, compound

Product 1

HCID 57191012HCID 57191012, compoundYield 100.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent3×HCID 65578Oxalyl chlorideSolvent

Procedure

In methylene chloride (24 ml), oxalyl chloride (0.40 ml) was dissolved. To the resulting solution, a solution of dimethyl sulfoxide (0.44 ml) in methylene chloride (1.6 ml) was added at -78° C., followed by stirring for 10 minutes. To the resulting solution, a solution of (2S,4S)-2-hydroxymethyl-4-(4-methoxybenzylthio)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (1 g) in methylene chloride (8 ml) was added dropwise at the same temperature, followed by stirring at -78° C. for 15 minutes and -50 to -60° C. for one hour. To the reaction mixture, triethylamine (2.4 ml) was added, followed by stirring at -14 to -15° C. for 20 minutes. To the reaction mixture, 1N hydrochloric acid was added to make the resulting solution acidic, followed by extraction with methylene chloride. The methylene chloride layer was washed with water and saline and then dried over anhydrous sodium sulfate. The solvent was distilled off, whereby (2S,4S)-2-formyl-4-(4-methoxybenzylthio)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (1 g) was obtained.

Workup

  1. stirringby stirring at -78° C. for 15 minutes and -50 to -60° C. for one hour
  2. stirringby stirring at -14 to -15° C. for 20 minutes
  3. extractionfollowed by extraction with methylene chloride
  4. washThe methylene chloride layer was washed with water and saline
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-77dcfeb45e0a4a65a372ecd92a4d3d15
Source dataset
uspto-grants-2000_07
Patent number
US06090802

Reaction notes

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