Water → HCID 67170495, compound

HRID 574852Notes

Reaction equation

HRID 574852 reaction equation
[C@H:1]12[CH2:7][C@H:4]([CH:5]=[CH:6]1)[CH2:3][CH:2]2[CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([S:16]([NH2:19])(=[O:18])=[O:17])=[CH:12][C:11]=1[N+:20]([O-:22])=[O:21].C[N+]1([O-])CC[O:27]CC1.[OH2:31]>O1CCCC1.O=[Os](=O)(=O)=O>[OH:31][C@H:5]1[C@@H:6]([OH:27])[C@@H:1]2[CH2:7][C@H:4]1[CH2:3][CH:2]2[CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([S:16]([NH2:19])(=[O:18])=[O:17])=[CH:12][C:11]=1[N+:20]([O-:22])=[O:21]

Participants

6

Reactant 3

HCID 962WaterHCID 82029Methyl morpholine oxideHCID 67169824HCID 67169824, compound

Product 1

HCID 67170495HCID 67170495, compound

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of EXAMPLE 201A (340 mg) in tetrahydrofuran (10 mL) and water (1 mL) was added N-methylmorpholine N-oxide (184 mg) and OsO4 (2.5% in 2-methyl-2-propanol) (1.05 mL). The reaction mixture was stirred overnight and purified by reverse phase HPLC to provide two isomers, which were temporarily assigned as EXAMPLE 203A and EXAMPLE 203B, respectively.

Workup

  1. custompurified by reverse phase HPLC
  2. customto provide two isomers, which

Sources & evidence

ORD record
ord-82de746afd994ea380a09e10e672cfb2
Source dataset
uspto-grants-2015_05
Patent number
US09034875B2

Reaction notes

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