HCID 70044251, compound → HCID 70041879, compound

HRID 847604Notes

Reaction equation

HRID 847604 reaction equation
[C:1]([NH:4][C@H:5]([C:9]([NH:11][C@H:12]([C:16]([NH:18][CH:19]([CH:27]([OH:54])[CH:28]([NH:36][C:37](=[O:53])[C@H:38]([CH:50]([CH3:52])[CH3:51])[NH:39][C:40](=[O:49])[C@H:41]([CH:46]([CH3:48])[CH3:47])[NH:42][C:43](=[O:45])[CH3:44])[CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:17])[CH:13]([CH3:15])[CH3:14])=[O:10])[CH:6]([CH3:8])[CH3:7])(=[O:3])[CH3:2]>CC(C)=O.[Cr](O)(O)(=O)=O>[C:1]([NH:4][C@H:5]([C:9]([NH:11][C@H:12]([C:16]([NH:18][CH:19]([C:27](=[O:54])[CH:28]([NH:36][C:37](=[O:53])[C@H:38]([CH:50]([CH3:52])[CH3:51])[NH:39][C:40](=[O:49])[C@H:41]([CH:46]([CH3:48])[CH3:47])[NH:42][C:43](=[O:45])[CH3:44])[CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:17])[CH:13]([CH3:14])[CH3:15])=[O:10])[CH:6]([CH3:7])[CH3:8])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 70044251HCID 70044251, compound

Product 1

HCID 70041879HCID 70041879, compoundYield 8.8%

Reagents, catalysts & solvents 2

HCID 24425Chromic AcidCatalystHCID 180AcetoneSolvent

Procedure

A solution of the resultant compound of Example 59 (0.056 mmol) in 10 ml of acetone was cooled to 0° C. and treated with 5 drops of aqueous chromic acid. After 1.25 h, the solution was quenched with 2-propanol and aqueous NaHCO3, filtered through Celite, extracted with 10% methanol in chloroform, and concentrated in vacuo. Flash chromatography using 7.5% methanol in chloroform gave 3.7 mg (9%) of the desired compound (Rf 0 39, 10% methanol in chloroform). Mass spectrum (M+H)+ =749.

Workup

  1. customthe solution was quenched with 2-propanol and aqueous NaHCO3
  2. filtrationfiltered through Celite
  3. extractionextracted with 10% methanol in chloroform
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-637cd8a250bf4f4683e788032dd2a3aa
Source dataset
uspto-grants-1992_08
Patent number
US05142056

Reaction notes

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