(S)-3-(2-((S)-1-(4-(hydroxymethyl)phenyl)ethylamino)pyrimidin-4-yl)-4-isopropyloxazolidin-2-one → 4-((S)-1-(4-((S)-4-isopropyl-2-oxooxazolidin-3-yl)pyrimidin-2-ylamino)ethyl)benzaldehyde

HRID 1850126Notes

Reaction equation

HRID 1850126 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]([NH:11][C:12]2[N:17]=[C:16]([N:18]3[C@@H:22]([CH:23]([CH3:25])[CH3:24])[CH2:21][O:20][C:19]3=[O:26])[CH:15]=[CH:14][N:13]=2)[CH3:10])=[CH:5][CH:4]=1>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH:23]([C@H:22]1[CH2:21][O:20][C:19](=[O:26])[N:18]1[C:16]1[CH:15]=[CH:14][N:13]=[C:12]([NH:11][C@H:9]([C:6]2[CH:5]=[CH:4][C:3]([CH:2]=[O:1])=[CH:8][CH:7]=2)[CH3:10])[N:17]=1)([CH3:24])[CH3:25]

Participants

4

Reactant 1

HCID 86730160(S)-3-(2-((S)-1-(4-(hydroxymethyl)phenyl)ethylamino)pyrimidin-4-yl)-4-isopropyloxazolidin-2-one

Product 1

HCID 867301594-((S)-1-(4-((S)-4-isopropyl-2-oxooxazolidin-3-yl)pyrimidin-2-ylamino)ethyl)benzaldehyde

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of (S)-3-(2-((S)-1-(4-(hydroxymethyl)phenyl)ethylamino)pyrimidin-4-yl)-4-isopropyloxazolidin-2-one (285 mg, 0.8 mmol) and manganese dioxide (2.78 g, 32 mmol, 40 equiv) in DCM (16 mL) was stirred at room temperature for 30 min. The solution was filtered through a pad of celite and washed with DCM. The filtrated was concentrated and used to next step without further purification.

Workup

  1. filtrationThe solution was filtered through a pad of celite
  2. washwashed with DCM
  3. concentrationThe filtrated was concentrated
  4. customused to next step without further purification

Sources & evidence

ORD record
ord-37fe43ff9140445886004e346fe7ccab
Source dataset
uspto-grants-2015_02
Patent number
US08957068B2

Reaction notes

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