Water → HCID 57114237, compound

HRID 346375Notes

Reaction equation

HRID 346375 reaction equation
[OH:1][C@H:2]1[CH2:6][N:5]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)=[O:8])[C@H:4]([CH2:20][N:21]([C:28]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][C:35]([N+:38]([O-:40])=[O:39])=[CH:34][CH:33]=2)=[O:29])[CH2:22][CH2:23][NH:24][C:25]([NH2:27])=O)[CH2:3]1.[CH3:41][S:42](Cl)(=[O:44])=[O:43].O.C(OCC)(=O)C>N1C=CC=CC=1>[C:25]([NH:24][CH2:23][CH2:22][N:21]([CH2:20][C@@H:4]1[CH2:3][C@@H:2]([O:1][S:42]([CH3:41])(=[O:44])=[O:43])[CH2:6][N:5]1[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])[C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][C:35]([N+:38]([O-:40])=[O:39])=[CH:34][CH:33]=1)=[O:29])#[N:27]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 57204048HCID 57204048, compound

Product 1

HCID 57114237HCID 57114237, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of (2S, 4R)-4-hydroxy-1-(4-nitrobenzyloxycarbonyl)-2-[N-(4-nitrobenzyloxycarbonyl)-N-(2-ureidoethyl)amino]methylpyrrolidine (1.75 g) in pyridine (17.5 ml) was added methanesulfonyl chloride (0.60 ml) at 0°~10° C. The mixture was stirred at the same temperature for 1 hour and at ambient temperature for 15 hours. The mixture was poured into a mixture of water (100 ml) and ethyl acetate (100 ml). The organic layer was washed in turn with 1N hydrochloric acid (100 ml×3), saturated sodium hydrogen carbonate (100 ml) and brine (100 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 (30 g) and eluted with a mixture of methanol and chloroform (1:99 v/v) to give (2S, 4R)-2-[N-{2-(cyanoamino)ethyl}-N-(4-nitrobenzyloxycarbonyl)aminomethyl]-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (1.53 g).

Workup

  1. washThe organic layer was washed in turn with 1N hydrochloric acid (100 ml×3), saturated sodium hydrogen carbonate (100 ml) and brine (100 ml)
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customto give a syrup
  5. washeluted with a mixture of methanol and chloroform (1:99 v/v)

Sources & evidence

ORD record
ord-a60c0a16e70049319d9087356a0413ec
Source dataset
uspto-grants-1991_10
Patent number
US05061804

Reaction notes

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