Water → HCID 70153490, compound

HRID 2296744Notes

Reaction equation

HRID 2296744 reaction equation
CC(C)=[O:3].O[S:6]([OH:9])(=O)=O.O=[Cr](=O)=O.S(=O)(=O)(O)O.[OH:19][CH2:20][CH2:21][CH:22]1[CH:28]=[CH:27][N:26]([C:29](=[O:51])[C:30]2[CH:35]=[CH:34][C:33]([NH:36][C:37](=[O:50])[C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=3[C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)=[CH:32][CH:31]=2)[C:25]2[CH:52]=[CH:53][CH:54]=[CH:55][C:24]=2S1.O>CC(C)=O>[C:20]([CH2:21][CH:22]1[CH:28]=[CH:27][N:26]([C:29](=[O:51])[C:30]2[CH:35]=[CH:34][C:33]([NH:36][C:37](=[O:50])[C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=3[C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)=[CH:32][CH:31]=2)[C:25]2[CH:52]=[CH:53][CH:54]=[CH:55][C:24]=2[S:6]1=[O:9])([OH:3])=[O:19]

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 18387436HCID 18387436, compoundHCID 131709961Jones' reagent

Product 1

HCID 70153490HCID 70153490, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

Excess Jones reagent (5.0 ml) prepared by a slow addition of concentrated sulfuric acid (150 ml) to a cold solution (0-5° C.) of CrO3 (180 g, 1.8M) in ice water (1.21) and stirred for one hour at 0° C., was slowly added to a cold mixture of Compound 17 as prepared in Example 3 (4.0 g, 7.8 mM) in acetone (60 ml). The resulting mixture was stirred at room temperature overnight. Water (100 ml) was then slowly added and the volatile solvents removed in vacuo. The aqueous mixture was extracted with ethyl acetate (2×100 ml). The combined EtOAc extracts were dried (MgSO4), filtered and evaporated in vacuo to give a crude product. Purification by flash column chromatography (EM silica gel 60; 10% EtOAc in CH2Cl2) gave the desired product as a white solid. m/z (MH+) 539.

Workup

  1. stirringThe resulting mixture was stirred at room temperature overnight
  2. customthe volatile solvents removed in vacuo
  3. extractionThe aqueous mixture was extracted with ethyl acetate (2×100 ml)
  4. dry with materialThe combined EtOAc extracts were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto give a crude product
  8. customPurification by flash column chromatography (EM silica gel 60; 10% EtOAc in CH2Cl2)

Sources & evidence

ORD record
ord-471a7947a94341278e8ac1d4f80ea33e
Source dataset
uspto-grants-2002_12
Patent number
US06489321B1

Reaction notes

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