HCID 70008201, compound → HCID 69612267, compound

HRID 412089Notes

Reaction equation

HRID 412089 reaction equation
[C:1]([NH:11][C@H:12]([C:17]([C@@H:19]([NH2:41])[CH:20]([OH:40])[CH:21]([NH:23][S:24]([C:27]1[CH:39]=[CH:38][C:30]2[O:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[C:29]=2[CH:28]=1)(=[O:26])=[O:25])[CH3:22])=[O:18])[CH2:13][CH:14]([CH3:16])[CH3:15])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[C:1]([NH:11][C@H:12]([C:17]([C@H:19]([NH2:41])[C:20](=[O:40])[CH:21]([NH:23][S:24]([C:27]1[CH:39]=[CH:38][C:30]2[O:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[C:29]=2[CH:28]=1)(=[O:25])=[O:26])[CH3:22])=[O:18])[CH2:13][CH:14]([CH3:16])[CH3:15])([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2]

Participants

4

Reactant 2

HCID 70008201HCID 70008201, compoundHCID 131709961Jones' reagent

Product 1

HCID 69612267HCID 69612267, compoundYield 30.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1-(Cbz-leucinyl)-amino-3-(2-dibenzofuransulfonamido)-(S)-butan-2-ol (240 mg, 0.4 mmol) was dissolved in acetone (2 ml). Jones reagent (0.5 ml, 1.5 M) was added dropwise and the reaction was stirred at RT overnight. The excess Jones reagent was then quenched with isopropanol (1.0 ml), then the reaction was diluted with EtOAc (20 ml) and was extracted with water (2×20 ml) to remove the inorganic salts. The combined organics were dried with magnesium sulfate, filtered, concentrated, and chromatographed (silica gel, 2-5% MeOH/methylene chloride) to give the tide compound as a white solid (70 mg, 29%). MS(ES) M−H−=578.

Workup

  1. customThe excess Jones reagent was then quenched with isopropanol (1.0 ml)
  2. additionthe reaction was diluted with EtOAc (20 ml)
  3. extractionwas extracted with water (2×20 ml)
  4. customto remove the inorganic salts
  5. dry with materialThe combined organics were dried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customchromatographed (silica gel, 2-5% MeOH/methylene chloride)

Sources & evidence

ORD record
ord-4e36f157871542309eb3398f2dc6e6d7
Source dataset
uspto-grants-2003_05
Patent number
US06562842B2

Reaction notes

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