Water → HCID 24829988, compound

HRID 1025354Notes

Reaction equation

HRID 1025354 reaction equation
[CH3:1][C:2]1[CH:26]=[N:25][CH:24]=[CH:23][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH2:18][C@@H:17](C(C)=C)[CH2:16][CH2:15][C:14]=2[CH3:22])=[CH:9][CH:8]=1)=[O:5].[CH:27]([OH:30])([CH3:29])[CH3:28].[OH2:31]>O=[Os](=O)(=O)=O>[OH:31][CH2:28][C@@:27]([C@@H:17]1[CH2:18][C:13]([C:10]2[CH:11]=[CH:12][C:7]([NH:6][C:4](=[O:5])[C:3]3[CH:23]=[CH:24][N:25]=[CH:26][C:2]=3[CH3:1])=[CH:8][CH:9]=2)=[C:14]([CH3:22])[CH2:15][CH2:16]1)([OH:30])[CH3:29]

Participants

5

Reactant 3

HCID 962WaterHCID 3776IsopropanolHCID 24829982HCID 24829982, compound

Product 1

HCID 24829988HCID 24829988, compound

Reagents, catalysts & solvents 1

HCID 30318Osmium TetroxideCatalyst

Procedure

A solution of Compound 3 (133 mg, 0.383 mmol) in 2:1 isopropylalcohol and water was stirred at room temperature. N-morpholine oxide (40 mg, 1 eq.) was added followed by a solution of OsO4 (3 mol %). The reaction was stirred for 18 hours, quenched with water and extracted with methylene chloride.

Workup

  1. customquenched with water
  2. extractionextracted with methylene chloride

Sources & evidence

ORD record
ord-d286c30f63d8486dbacd70dfb151a48d
Source dataset
uspto-grants-2014_05
Patent number
US08729069B2

Reaction notes

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