1,2-Dichloroethane → HCID 12113746, compound

HRID 1166060Notes

Reaction equation

HRID 1166060 reaction equation
[CH3:1][C:2]([CH3:46])=[CH:3][CH2:4][CH2:5][C@@:6]1([CH3:45])[O:15][C:14]2[C:13]([CH2:16][CH:17]=[C:18]([CH3:20])[CH3:19])=[C:12]3[O:21][C@@:22]45[C@@:32]6([CH2:37]/[CH:38]=[C:39](\[C:41]([OH:43])=[O:42])/[CH3:40])[O:33][C:34]([CH3:36])([CH3:35])[C@@H:23]4[CH2:24][C@H:25]([C:30]6=[O:31])[CH:26]=[C:27]5[C:28](=[O:29])[C:11]3=[C:10]([OH:44])[C:9]=2[CH:8]=[CH:7]1.[CH2:47](Cl)CCl.CO.O>CN(C1C=CN=CC=1)C.C1COCC1>[CH3:1][C:2]([CH3:46])=[CH:3][CH2:4][CH2:5][C@@:6]1([CH3:45])[O:15][C:14]2[C:9](=[C:10]([OH:44])[C:11]3[C:28](=[O:29])[C:27]4[C@@:22]5([C@@:32]6([CH2:37]/[CH:38]=[C:39](\[C:41]([O:43][CH3:47])=[O:42])/[CH3:40])[O:33][C:34]([CH3:35])([CH3:36])[C@@H:23]5[CH2:24][C@H:25]([C:30]6=[O:31])[CH:26]=4)[O:21][C:12]=3[C:13]=2[CH2:16][CH:17]=[C:18]([CH3:19])[CH3:20])[CH:8]=[CH:7]1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 887MethanolHCID 962WaterHCID 9852185Gambogic acid

Product 1

HCID 12113746HCID 12113746, compoundYield 95.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of gambogic acid (200 mg, 0.32 mmol), DMAP (78 mg, 0.64 mmol), EDC (123 mg, 0.64 mmol) and methanol (102 mg, 3.2 mmol) in THF (5 mL) was stirred at room temperature for 3 h. The solution was poured into water (10 mL) and was extracted with ethyl acetate (3×10 mL). The combined organic layer was dried and concentrated to give the crude product, which was purified by chromatography (SiO2, EtOAc/Hexane 1:5) to give the title compound (196 mg, 95%). 1H NMR (CDCl3): 12.85 (s, 1H), 7.54 (d, J=6.9 Hz, 1H), 6.67 (d, J=10.5 Hz, 1H), 5.94 (t, J=6 Hz, 1H), 5.43 (d, J=10.2 Hz, 1H), 5.05 (m, 2H), 3.49 (m, 1H), 3.43 (s, 3H), 3.35-3.10 (s, 2H), 3.00 (t, J=7.2 Hz, 1H), 2.52 (d, J=10.2 Hz, 1H), 2.32 (quar, J1=4.8 Hz, 1H), 2.02 (m, 1H), 1.74 (s, 3H), 1.69 (s, 3H), 1.67-1.64 (m, 9H), 1.55 (s, 3H), 1.44 (s, 3H), 1.29 (s, 3H).

Workup

  1. extractionwas extracted with ethyl acetate (3×10 mL)
  2. customThe combined organic layer was dried
  3. concentrationconcentrated
  4. customto give the crude product, which
  5. customwas purified by chromatography (SiO2, EtOAc/Hexane 1:5)

Sources & evidence

ORD record
ord-a897b7e0d24b43a3a7c77443220c9962
Source dataset
uspto-grants-2003_09
Patent number
US06613762B2

Reaction notes

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