Water → HCID 57010773, compound

HRID 975658Notes

Reaction equation

HRID 975658 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([OH:12])[CH2:9][C@H:8]1[CH2:13][N:14]1[CH2:19][CH2:18][N:17]([CH:20]=[O:21])[CH2:16][C:15]1=[O:22])=[O:6])[CH:2]=[CH2:3].C(N(CC)CC)C.[CH3:30][S:31](Cl)(=[O:33])=[O:32].O>C(OCC)(=O)C>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([O:12][S:31]([CH3:30])(=[O:33])=[O:32])[CH2:9][C@H:8]1[CH2:13][N:14]1[CH2:19][CH2:18][N:17]([CH:20]=[O:21])[CH2:16][C:15]1=[O:22])=[O:6])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 57145713HCID 57145713, compound

Product 1

HCID 57010773HCID 57010773, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2S,4R)-1-allyloxycarbonyl-2-(4-formyl-2-oxopiperazin-1-yl) methyl-4-hydroxypyrrolidine (11.38 g) in ethyl acetate (110 ml) were added triethylamine (5.6 ml) and methanesulfonyl chloride (3.11 ml) under ice-cooling with stirring, and the mixture was stirred at the same temperature for 1 hour. To the mixture was added water and the mixture was evaporated in vacuo. To the residue was added tetrahydrofuran, and the mixture was stirred at 50° C. for 20 minutes. The mixture was filtered and the filtrate was dried over anhydrous magnesium sulfate, and evaporated in vacuo to give (2S,4R)-1-allyloxycarbonyl-2-(4-formyl-2-oxopiperazin-1-yl) methyl-4-(methanesulfonyloxy)pyrrolidine (14.2 g).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at the same temperature for 1 hour
  3. customthe mixture was evaporated in vacuo
  4. additionTo the residue was added tetrahydrofuran
  5. stirringthe mixture was stirred at 50° C. for 20 minutes
  6. filtrationThe mixture was filtered
  7. dry with materialthe filtrate was dried over anhydrous magnesium sulfate
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-a6bbfc49b90f483fb4bfd5e8326e551c
Source dataset
uspto-grants-1997_03
Patent number
US05608056

Reaction notes

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