HCID 70008201, compound → HCID 69612267, compound

HRID 1594964Notes

Reaction equation

HRID 1594964 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 (2×30 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 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 (2×30 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-49f7616fdd5d4f37b17b907ac7bc1a8b
Source dataset
uspto-grants-2001_09
Patent number
US06284777B1

Reaction notes

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