Hydrochloric Acid → HCID 54118143, compound

HRID 620781Notes

Reaction equation

HRID 620781 reaction equation
C(OC([N:11]1[CH2:15][C@H:14]([O:16][S:17]([CH3:20])(=[O:19])=[O:18])[CH2:13][C@H:12]1[CH2:21][O:22][CH2:23][CH2:24][NH:25][C:26]([NH2:28])=[O:27])=O)C1C=CC=CC=1.Cl.[H][H]>[Pd].CO>[CH3:20][S:17]([O:16][C@H:14]1[CH2:15][NH:11][C@H:12]([CH2:21][O:22][CH2:23][CH2:24][NH:25][C:26]([NH2:28])=[O:27])[CH2:13]1)(=[O:18])=[O:19]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 53918022HCID 53918022, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 54118143HCID 54118143, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (2S,4R)-1-benzyloxycarbonyl-4-methanesulfonyloxy-2-[(2-ureidoethyl)oxymethyl]pyrrolidine (13.25 g), concentrated hydrochloric acid (3 ml), methanol (150 ml) and 10% palladium on carbon (0.5 g) was stirred under atmospheric pressure of hydrogen at ambient temperature for 4 hours. The catalyst was filtered off and the filtrate was concentrated under reduced pressure to give (2S,4R)-4-methanesulfonyloxy-2-[(2-ureidoethyl)oxymethyl]pyrrolidine. To a solution of the compound obtained above in a mixture of tetrahydrofuran (100 ml) and water (100 ml) was dropwise added a solution of allyl chloroformate (3.75 ml) in tetrahydrofuran (30 ml) under ice-cooling with stirring, keeping the pH between 8.5-9.5 with 4N aqueous sodium hydroxide. The mixture was stirred at the same condition for 1 hour and extracted with ethyl acetate (100 ml×2). The organic layer was dried over magnesium sulfate and evaporated under reduced pressure to give a syrup. The syrup was subjected to a column chromatography on silica gel (150 g) and eluted with a mixture of methanol and chloroform (2:98 and then 4:96 V/V) to give (2S,4R)-1-allyloxycarbonyl-4-methanesulfonyloxy-2-[(2-ureidoethyl)oxymethyl]pyrrolidine (11.02 g).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-20ff3832399848bea1dfc63da1f1fc65
Source dataset
uspto-grants-1989_04
Patent number
US04822787

Reaction notes

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