HCID 72707772, compound → HCID 72707773, compound

HRID 541112Notes

Reaction equation

HRID 541112 reaction equation
[CH2:1]([O:8][C@H:9]([C@@H:22]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH2:23][O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C@H:10]([NH:13][C@@H:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:15])[CH2:11][OH:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)=[O:42].OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[CH2:1]([O:8][C@H:9]([C@@H:22]([O:32][CH2:33][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)[CH2:23][O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C@H:10]([NH:13][C@@H:14]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[CH3:15])[C:11]([OH:42])=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 72707772HCID 72707772, compoundHCID 131709961Jones' reagent

Product 1

HCID 72707773HCID 72707773, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (2R,3S,4S)-3,4,5-tris(benzyloxy)-2-(((R)-1-phenylethyl)amino)pentan-1-ol (110 mg, 0.209 mmol) in acetone (2 mL, 0.1 M) was added Jones reagent (0.21 mL, 0.522 mmol, 2.5 M solution in H2O) at 0° C. The reaction mixture was stirred for 4 hrs at 0° C., quenched with isopropyl alcohol and filtered through a pad of celite and washed with CH2Cl2. The reaction mixture was partitioned between CH2Cl2 and water. The aqueous layer was extracted with CH2Cl2 and the combined organic layer was washed with brine, dried over MgSO4, filtered through a pad of celite, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography with ethyl acetate/hexane (1/2) to CH2Cl2/MeOH (20/1) to afford the title product. Yield: 59 mg (0.11 mmol, 52%); white solid.

Workup

  1. customquenched with isopropyl alcohol
  2. filtrationfiltered through a pad of celite
  3. washwashed with CH2Cl2
  4. customThe reaction mixture was partitioned between CH2Cl2 and water
  5. extractionThe aqueous layer was extracted with CH2Cl2
  6. washthe combined organic layer was washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered through a pad of celite
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4d72f8e3e20147efaa5f027a408574aa
Source dataset
uspto-grants-2014_10
Patent number
US08871950B1

Reaction notes

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