Hydrochloric Acid → HCID 54136579, compound

HRID 975659Notes

Reaction equation

HRID 975659 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([O:12][S:13]([CH3:16])(=[O:15])=[O:14])[CH2:9][C@H:8]1[CH2:17][N:18]1[CH2:23][CH2:22][N:21](C=O)[CH2:20][C:19]1=[O:26])=[O:6])[CH:2]=[CH2:3].Cl.[Na]>CO>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([O:12][S:13]([CH3:16])(=[O:15])=[O:14])[CH2:9][C@H:8]1[CH2:17][N:18]1[CH2:23][CH2:22][NH:21][CH2:20][C:19]1=[O:26])=[O:6])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5360545SodiumHCID 57010773HCID 57010773, compound

Product 1

HCID 54136579HCID 54136579, compoundYield 49.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of (2S,4R)-1-allyloxycarbonyl-2-(4-formyl-2-oxopiperazin-1-yl) methyl-4-(methanesulfonyloxy)pyrrolidine (14.2 g) in methanol (60 ml) was added conc. hydrochloric acid (12.2 ml) under ice cooling with stirring, and the mixture was stirred at the same temperature for 10 hours. The mixture was cooled to 5° C. and 28% sodium methoxidemethanol solution (28.2 ml) was added to it. The mixture was filtered, and the filtrate was evaporated in vacuo. To the residue was added chloroform. The mixture was dried over anhydrous magnesium sulfate and evaporated in vacuo to give (2S,4R)-1-allyloxycarbonyl-2-(2-oxopiperazin-1-yl) methyl-4-(methanesulfonyloxy)pyrrolidine (6.54 g).

Workup

  1. stirringthe mixture was stirred at the same temperature for 10 hours
  2. filtrationThe mixture was filtered
  3. customthe filtrate was evaporated in vacuo
  4. additionTo the residue was added chloroform
  5. dry with materialThe mixture was dried over anhydrous magnesium sulfate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-17453d55002e410f908a9bf6e8235920
Source dataset
uspto-grants-1997_03
Patent number
US05608056

Reaction notes

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