Oxygen → Qing Hau Sau

HRID 1746629

Reaction equation

HRID 1746629 reaction equation
[CH3:1][C@H:2]1[C@@H:7]2[CH2:8][CH2:9][C:10]([CH3:12])=[CH:11][C@@H:6]2[C@H:5]([C@H:13]([C:15]([OH:17])=[O:16])[CH3:14])[CH2:4][CH2:3]1.C1C=CC(C2C3NC(C(C4C=CC=CC=4)=C4C=CC(=C(C5C=CC=CC=5)C5C=CC(=C(C6C=CC=CC=6)C6C=CC=2N=6)N=5)N4)=CC=3)=CC=1.[O:66]=[O:67].FC(F)(F)C(O)=[O:71]>C1(C)C=CC=CC=1>[CH3:1][C@H:2]1[C@@H:7]2[CH2:8][CH2:9][C@:10]3([CH3:12])[O:66][O:67][C@:6]42[C@H:5]([C@@H:13]([CH3:14])[C:15]([O:17][C@@H:11]4[O:71]3)=[O:16])[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 977OxygenHCID 6422Trifluoroacetic acid2×HCID 701865,10,15,20-Tetraphenyl-21,22-dihydroporphyrinHCID 11020893Dihydroartemisinic acid

Product 1

HCID 9838675Qing Hau SauYield 62%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

The feed was a solution of dihydroartemisinic acid at a concentration of 0.5 mol/L and the photosensitizer tetraphenylporphyrin at a concentration of 1 mmol/L in toluene (2.95 g dihydroartemisinic acid and 15 mg tetraphenylporphyrin, total volume 25 mL, volumetric flask). The feed was introduced at a flow rate of 1.25 mL/min and the oxygen flow adjusted to 5 mL/min. The solution of trifluoroacetic acid injected into the output stream of the photochemical reactor contains 1.93 mL trifluoroacetic acid filled up to 20 ml with toluene (1.25 M, volumetric flask). The output stream showed a conversion of 89% yielding 62% of the desired artemisinin with a selectivity of 70% (NMR of crude).

Workup

  1. additionThe feed was introduced at a flow rate of 1.25 mL/min

Sources & evidence

ORD record
ord-056272f6b877429483a9953680863e93
Source dataset
uspto-grants-2015_10
Patent number
US09150535B2

Linked notes

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