Oxalic acid dihydrate → HCID 86744299, compound

HRID 1088989Notes

Reaction equation

HRID 1088989 reaction equation
[C:1]([NH:3][CH2:4][CH2:5][N:6]([CH2:20][C@@H:21]1[CH2:25][C@@H:24]([O:26][S:27]([CH3:30])(=[O:29])=[O:28])[CH2:23][N:22]1[C:31]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][C:38]([N+:41]([O-:43])=[O:42])=[CH:37][CH:36]=1)=[O:32])[C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=1)=[O:8])#[N:2].O.O.C(O)(=O)C(O)=[O:48]>CC(C)=O.C(OCC)(=O)C>[CH3:30][S:27]([O:26][C@H:24]1[CH2:23][N:22]([C:31]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][C:38]([N+:41]([O-:43])=[O:42])=[CH:37][CH:36]=2)=[O:32])[C@H:21]([CH2:20][N:6]([C:7]([O:9][CH2:10][C:11]2[CH:12]=[CH:13][C:14]([N+:17]([O-:19])=[O:18])=[CH:15][CH:16]=2)=[O:8])[CH2:5][CH2:4][NH:3][C:1]([NH2:2])=[O:48])[CH2:25]1)(=[O:28])=[O:29]

Participants

5

Reactant 2

HCID 61373Oxalic acid dihydrateHCID 57114237HCID 57114237, compound

Product 1

HCID 86744299HCID 86744299, compoundYield 91.4%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2S, 4R)-2-[N-{2-(cyanoamino)ethyl}-N-(4-nitrobenzyloxycarbonyl)aminomethyl]-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (1.52 g) in acetone (30 ml) was added oxalic acid dihydrate (1.92 g) at ambient temperature. The mixture was stirred at the same temperature for 18 hours. Acetone was removed by evaporation to give a residue. A suspension of the syrup in ethyl acetate (100 ml) was washed in turn with 1N aqueous sodium hydroxide (50 ml×2), water (50 ml) and brine (50 ml), dried over magnesium sulfate and concentrated under reduced pressure to give a syrup. The syrup was subjected to a column chromatography on silica gel (20 g) and eluted with a mixture of methanol and chloroform (2:98 v/v) to give (2S, 4R)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)-2-[N-(4-nitrobenzyloxycarbonyl)-N-(2-ureidoethyl)aminomethyl]pyrrolidine (1.43 g).

Workup

  1. customAcetone was removed by evaporation
  2. customto give a residue
  3. washwas washed in turn with 1N aqueous sodium hydroxide (50 ml×2), water (50 ml) and brine (50 ml)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give a syrup
  7. washeluted with a mixture of methanol and chloroform (2:98 v/v)

Sources & evidence

ORD record
ord-4600873aa88e459399da88ad2ac27b94
Source dataset
uspto-grants-1990_10
Patent number
US04963543

Reaction notes

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