HCID 70008201, compound → HCID 69612267, compound

HRID 610410Notes

Reaction equation

HRID 610410 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.CCOC(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

5

Reactant 2

HCID 70008201HCID 70008201, compoundHCID 131709961Jones' reagent

Product 1

HCID 69612267HCID 69612267, compoundYield 30.2%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

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 as stirred at RT overnight. The excess Jones reagent was then quenched with isopropanol (1.0 ml), then the reaction as 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 title compound as a white solid (70 mg, 29%). MS(ES) M-H+ =578.

Workup

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

Sources & evidence

ORD record
ord-5c4f329b83a84eaa936f24a1d3ff18bc
Source dataset
uspto-grants-1999_12
Patent number
US05998470

Reaction notes

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