Propanoic acid, 2-[(methylsulfonyl)oxy]-, (R)- → t-butyl (4S)-1-methyl-3-[(2R)-2-(methanesulfonyloxy)-propionyl]-2-oxoimidazolidine-4carboxylate

HRID 2050615Notes

Reaction equation

HRID 2050615 reaction equation
[CH3:1][S:2]([O:5][C@H:6]([CH3:10])[C:7](O)=[O:8])(=[O:4])=[O:3].[CH3:11][N:12]1[CH2:16][C@@H:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[NH:14][C:13]1=[O:24]>>[CH3:11][N:12]1[CH2:16][C@@H:15]([C:17]([O:19][C:20]([CH3:22])([CH3:21])[CH3:23])=[O:18])[N:14]([C:7](=[O:8])[C@H:6]([O:5][S:2]([CH3:1])(=[O:4])=[O:3])[CH3:10])[C:13]1=[O:24]

Participants

3

Reactant 2

HCID 12761548Propanoic acid, 2-[(methylsulfonyl)oxy]-, (R)-HCID 13053976tert-Butyl (4S)-1-methyl-2-oxoimidazolidine-4-carboxylate

Product 1

HCID 14801858t-butyl (4S)-1-methyl-3-[(2R)-2-(methanesulfonyloxy)-propionyl]-2-oxoimidazolidine-4carboxylateYield 75.8%

Procedure

D-lactic acid O-mesylate, namely (2R)-2-(methanesulfonyloxy)propionic acid (2.5 g) and t-butyl (4S)-1-methyl-2-oxoimidazolidine-4-carboxylate (3.42 g) were treated similarly as in Example 1 - (1), and the crude product was purified by silica gel chromatography (chloroform:ethyl acetate=1:2) and crystallized from n-hexane to give t-butyl (4S)-1-methyl-3-[(2R)-2-(methanesulfonyloxy)-propionyl]-2-oxoimidazolidine-4carboxylate (3.95 g). Yield: 75.8%., m.p.: 97°-100° C.

Workup

  1. customthe crude product was purified by silica gel chromatography (chloroform:ethyl acetate=1:2)
  2. customcrystallized from n-hexane

Sources & evidence

ORD record
ord-f3ef8e98c2b44b8e806f83250b2254d7
Source dataset
uspto-grants-1991_05
Patent number
US05013845

Reaction notes

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