1,2-Dichloroethane → HCID 12113746, compound

HRID 990699Notes

Reaction equation

HRID 990699 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-abb9be05319a4d2284a0a85b5c863d8b
Source dataset
uspto-grants-2002_10
Patent number
US06462041B1

Reaction notes

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