Sodium Bicarbonate → 21-Deoxyconcanolide A

HRID 976032Notes

Reaction equation

HRID 976032 reaction equation
O.C1(C)C(S(O)(=O)=O)=CC=CC=1.[CH3:13][CH2:14][C@@H:15]1[C@H:33]([OH:34])[C@H:32]([CH3:35])[CH:31]=[C:30]([CH3:36])[CH:29]=[C:28]([O:37][CH3:38])[C:26](=[O:27])[O:25][C@H:24]([C@H:39]([C@@H:41]([OH:67])[C@@H:42]([C@@H:44]2[O:49][C@H:48](/[CH:50]=[CH:51]/[CH3:52])[C@@H:47]([CH3:53])[C@H:46]([O:54][C@@H]3O[C@H](C)[C@@H](OC(N)=O)[C@H](O)C3)[CH2:45]2)[CH3:43])[CH3:40])[C@@H:23]([O:68][CH3:69])[CH:22]=[CH:21][CH:20]=[C:19]([CH3:70])[CH2:18][C@@H:17]([CH3:71])[C@@H:16]1[OH:72].C([O-])(O)=O.[Na+]>CC#N.O>[CH3:13][CH2:14][C@@H:15]1[C@H:33]([OH:34])[C@H:32]([CH3:35])[CH:31]=[C:30]([CH3:36])[CH:29]=[C:28]([O:37][CH3:38])[C:26](=[O:27])[O:25][C@H:24]([C@H:39]([C@@H:41]([OH:67])[C@@H:42]([C@@H:44]2[O:49][C@H:48](/[CH:50]=[CH:51]/[CH3:52])[C@@H:47]([CH3:53])[C@H:46]([OH:54])[CH2:45]2)[CH3:43])[CH3:40])[C@@H:23]([O:68][CH3:69])[CH:22]=[CH:21][CH:20]=[C:19]([CH3:70])[CH2:18][C@@H:17]([CH3:71])[C@@H:16]1[OH:72]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 1111555021-deoxyconcanamycin AHCID 124969952-Methylbenzenesulfonic acid hydrate

Product 1

HCID 1107245421-Deoxyconcanolide AYield 32.8%

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Conditions

Temperature
38 °C

Procedure

350 mg (1.83 mmol, 3 equiv.) of toluenesulfonic acid monohydrate (recrystallised from CHCl3) are added to a solution of 467 mg of 21-deoxyconcanamycin A (0.55 mmol) in 55 ml of CH3CN/H2O (5:1) and the reaction mixture is stirred at 38° C. for 12 hours. For working-up, the reaction mixture is cooled to 0° C. and 50 ml of saturated NaHCO3 solution are added; the organic solvent is removed in vacuo and the aqueous phase is extracted with CHCl3. TLC monitoring on silica gel (eluant: EtOAc/hexane 1:1) revealed two new zones in addition to the starting material at the starting spot. Column chromatography on silica gel (gradient EtOAc/hexane, 1:1 EtOAc) yields 63 mg (22% of the conversion) of 16-demethyl-21-deoxyconcanolide A, 122 mg of 21-deoxyconcanolide A (42% of the conversion) and 105 mg of starting material.

Workup

  1. temperaturethe reaction mixture is cooled to 0° C.
  2. customthe organic solvent is removed in vacuo
  3. extractionthe aqueous phase is extracted with CHCl3
  4. additionin addition to the starting material at the starting spot

Sources & evidence

ORD record
ord-776ff438ac554e8bb7701ad8afa29e5e
Source dataset
uspto-grants-1997_03
Patent number
US05610178

Reaction notes

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