Acetic Acid → HCID 11050687, compound

HRID 1199735Notes

Reaction equation

HRID 1199735 reaction equation
[CH3:1]/[CH:2]=[C:3](/[C:5]([O:7][C@@H:8]1[C@:16]23[C@H:20]([C@@:21]([C@:25]45[O:30][C@@:29]4([CH3:31])[C@H:28]4[C@:32]6([OH:38])[C@H:36]([O:37][C@@H:26]5[CH2:27]4)[O:35][CH:34]=[CH:33]6)([CH3:24])[C@H:22]([OH:23])[C@H:14]4[C@H:15]2[C@:11]([C:44]([O:46][CH3:47])=[O:45])([CH2:12][O:13]4)[C@H:10]([O:48]C(C)=O)[CH2:9]1)[C@@:19]([OH:43])([C:39]([O:41][CH3:42])=[O:40])[O:18][CH2:17]3)=[O:6])\[CH3:4].CO.C[O-].[Na+].C(O)(=O)C>O>[CH3:1]/[CH:2]=[C:3](/[C:5]([O:7][C@@H:8]1[C@:16]23[C@H:20]([C@@:21]([C@:25]45[O:30][C@@:29]4([CH3:31])[C@@H:28]4[C@:32]6([OH:38])[C@H:36]([O:37][C@H:26]5[CH2:27]4)[O:35][CH:34]=[CH:33]6)([CH3:24])[C@H:22]([OH:23])[C@H:14]4[C@H:15]2[C@:11]([C:44]([O:46][CH3:47])=[O:45])([CH2:12][O:13]4)[C@H:10]([OH:48])[CH2:9]1)[C@@:19]([OH:43])([C:39]([O:41][CH3:42])=[O:40])[O:18][CH2:17]3)=[O:6])\[CH3:4]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 10942334Sodium MethoxideHCID 44584063HCID 44584063, compound3×

Product 1

HCID 11050687HCID 11050687, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

15.8 mg. azadirachtin A (2.2×10-5 mole) were dissolved in 100 μl. methanol. To this solution were added three times 100 μl. amounts of a methanolic solution of sodium methylate (0.6 g. sodium in 50 ml. methanol). After each addition of 100 μl. methylate solution, there was a pause of 2 minutes and then a testing with HPLC whether azadirachtin A was still present. After the disappearance of azadirachtin A, the reaction mixture was neutralised with acetic acid, diluted with water and extracted with chloroform. The purification from by-products took place by semipreparative HPLC on a 20 cm. RP-18 column of 9 mm. internal diameter, using the elution agent methanol/ water (2:3 v/v); detection at 215 nm; yield 2.4 mg. (15.2% of theory).

Workup

  1. additionTo this solution were added three times 100 μl
  2. additionAfter each addition of 100 μl
  3. customa pause of 2 minutes
  4. extractionextracted with chloroform
  5. customThe purification from by-products

Sources & evidence

ORD record
ord-00274e5047a44cf585f49defd3f399b6
Source dataset
uspto-grants-1990_02
Patent number
US04902713

Reaction notes

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