tert-Butanol → HCID 18428501, compound

HRID 1279557Notes

Reaction equation

HRID 1279557 reaction equation
[CH:1]([CH:3]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:4][CH2:5][CH2:6][CH:7]1[CH:11]([CH3:12])[CH2:10][C:9](=[O:13])[NH:8]1)=[CH2:2].C[N+]1([O-])CC[O:26]CC1.CC(O)(C)C.[O-]S(S([O-])=O)=O.[Na+].[Na+].CC(C)=O.[OH2:47]>O=[Os](=O)(=O)=O.O>[OH:47][CH:1]([CH:3]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:4][CH2:5][CH2:6][CH:7]1[CH:11]([CH3:12])[CH2:10][C:9](=[O:13])[NH:8]1)[CH2:2][OH:26]

Participants

8

Reactant 5

HCID 6386tert-ButanolHCID 24489Sodium DithioniteHCID 82029Methyl morpholine oxideHCID 18366337Propan-2-one--water (1/1)HCID 18428617HCID 18428617, compound

Product 1

HCID 18428501HCID 18428501, compound

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent

Procedure

To a stirring solution of the compound from EXAMPLE 259 (3.3 mmol) in 80 mL of acetone:H2O (3:1) is added N-methylmorpholine N-oxide (0.64 g, 4.8 mmol) and 2.5% OsO4 in t-BuOH (3.4 mL, 3.4 mmol). After 18 h, 120 mL of H2O, 8 g of celite, and 1.6 g Na2S2O4 is added to the reaction. The reaction is filtered through a pad of wet celite. To the filtrate is added 200 mL of 1M KHSO4. The filtrate is extracted with 3×200 mL EtOAc. The combined organic layers are dried, filtered, and stripped. The residue is purified by chromatography to yield the title compound.

Workup

  1. filtrationThe reaction is filtered through a pad of wet celite
  2. additionTo the filtrate is added 200 mL of 1M KHSO4
  3. extractionThe filtrate is extracted with 3×200 mL EtOAc
  4. customThe combined organic layers are dried
  5. filtrationfiltered
  6. customThe residue is purified by chromatography

Sources & evidence

ORD record
ord-99c0fc4eea75456592ff73fecb70eb49
Source dataset
uspto-grants-2002_09
Patent number
US06448286B1

Reaction notes

Loading…