Water → 3-[N-Tert-butoxycarbonyl-4(S)-(3-carboxy-2,2-dimethylpropyl)-2,2-dimethyl-1,3-oxazolidin-5(S)-yl]-2(R)-but-2-enyl-propionic acid (N-butyl)amide

HRID 863329Notes

Reaction equation

HRID 863329 reaction equation
[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[CH2:22]([NH:26][C:27](=[O:55])[C@H:28]([CH2:51][CH:52]=[CH:53][CH3:54])[CH2:29][C@@H:30]1[O:34][C:33]([CH3:36])([CH3:35])[N:32]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[C@H:31]1[CH2:44][C:45]([CH3:50])([CH3:49])[CH2:46][CH2:47][OH:48])[CH2:23][CH2:24][CH3:25].[OH2:56]>CN(C)C=O>[CH2:22]([NH:26][C:27](=[O:55])[C@H:28]([CH2:51][CH:52]=[CH:53][CH3:54])[CH2:29][C@@H:30]1[O:34][C:33]([CH3:36])([CH3:35])[N:32]([C:37]([O:39][C:40]([CH3:41])([CH3:42])[CH3:43])=[O:38])[C@H:31]1[CH2:44][C:45]([CH3:50])([CH3:49])[CH2:46][C:47]([OH:56])=[O:48])[CH2:23][CH2:24][CH3:25]

Participants

5

Reactant 3

HCID 962WaterHCID 2724130Cornforth reagent2×HCID 867521183-[N-tert-butoxycarbonyl-4(S)-(4-hydroxy-2,2-dimethylbutyl)-2,2-dimethyl-1,3-oxazolidin-5(S)-yl]-2(R)-but-2-enyl-propionic acid (N-butyl)amide

Product 1

HCID 867521173-[N-Tert-butoxycarbonyl-4(S)-(3-carboxy-2,2-dimethylpropyl)-2,2-dimethyl-1,3-oxazolidin-5(S)-yl]-2(R)-but-2-enyl-propionic acid (N-butyl)amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 809 mg of pyridinium dichromate in 2 ml of N,N-dimethylformamide is added dropwise via a cannula to a solution of 290 mg of 3-[N-tert-butoxycarbonyl-4(S)-(4-hydroxy-2,2-dimethylbutyl)-2,2-dimethyl-1,3-oxazolidin-5(S)-yl]-2(R)-but-2-enyl-propionic acid (N-butyl)amide in 2 ml of N,N-dimethylformamide at room temperature under argon. After 23 h, a further 238 mg of pyridinium dichromate are added. After a total of 29 h, the reaction mixture is poured into water, extracted with diethyl ether (3 times), dried (Na2SO4) and concentrated. Purification over silica gel (mobile phase P) gives the title compound: Rf (P)=0.48; FAB-MS: (M+H)+ =497.

Workup

  1. extractionextracted with diethyl ether (3 times)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customPurification over silica gel (mobile phase P)

Sources & evidence

ORD record
ord-ccc7354e476d4edb95ffb2f783cded73
Source dataset
uspto-grants-1998_02
Patent number
US05719141

Reaction notes

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