Hydrochloric Acid → HCID 23643972, compound

HRID 713678Notes

Reaction equation

HRID 713678 reaction equation
Cl.[CH:2]1[C:7](/[CH:8]=[C:9]2\[C@@H:10](C3C=C(O)C=C(O)C=3)[C@H:11](C3C=CC(O)=CC=3)[C:12]3[C:17]\2=[CH:16][C:15]([OH:18])=[CH:14][C:13]=3[OH:19])=[CH:6][CH:5]=[C:4]([OH:35])[CH:3]=1>CO>[CH:6]1[C:7]([CH2:8][C:9]2[C:17]3[C:12](=[C:13]([OH:19])[CH:14]=[C:15]([OH:18])[CH:16]=3)[C@H:11]([C:17]3[CH:16]=[C:15]([OH:18])[CH:14]=[C:13]([OH:19])[CH:12]=3)[C:10]=2[C:7]2[CH:2]=[CH:3][C:4]([OH:35])=[CH:5][CH:6]=2)=[CH:2][CH:3]=[C:4]([OH:35])[CH:5]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 5318096Cyphostemmin B

Product 1

HCID 23643972HCID 23643972, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Concentrated HCl (50 mL, 0.600 mmol, 5.5 equiv.) was added to a solution of ampelopsin D (2, 5.0 mg, 0.110 mmol, 1.0 equiv) in MeOH (0.5 mL) at 25° C., and the resultant mixture was stirred at 80° C. for 12 h. Upon completion, the reaction mixture was quenched with water (3 mL) and extracted with EtOAc (3×10 mL). The combined organic layers were then washed with water (5 mL) and brine (5 mL), dried (MgSO4), and concentrated. The resulted light yellow product was purified by flash column chromatography (silica gel, CH2Cl2/MeOH, 9:1) to give isoampelopsin D 17 (4.8 mg, 96%) as a colorless oil. 17: Rf=0.13 (silica gel, CH2Cl2/MeOH, 9:1); IR (film) νmax 3411, 2810, 1680, 1628, 1511, 1443, 1371, 1333, 1206, 1149, 1055, 1006, 833; 1H NMR (300 MHz, methanol-d4) δ 7.11 (d, J=8.4 Hz, 2H), 7.07 (d, J=8.7 Hz, 2H), 6.73 (d, J=8.7 Hz, 2H), 6.66 (d, J=8.7 Hz, 2H), 6.17 (d, J=2.1 Hz, 1H), 6.06 (d, J=1.5 Hz, 1H), 6.06 (d, J=2.1 Hz, 2H), 5.99 (t, J=2.1 Hz, 1H), 4.80 (s, 1H), 3.84 (s, 2H); 13C NMR (75 MHz, methanol-d4) δ 158.9, 158.7, 157.5, 156.5, 154.0, 150.4, 149.9, 144.0, 136.6, 132.1, 131.1, 130.2, 128.9, 125.4, 116.3, 115.8, 108.1, 101.4, 100.7, 56.7, 32.2; HRMS (MALDI-FTMS) calcd for C28H22O6+[M+]454.1416. found 454.1428. All spectroscopic data for this synthetic material match those reported by Niwa and co-workers for natural isoampelopsin (15) [22].

Workup

  1. customUpon completion, the reaction mixture was quenched with water (3 mL)
  2. extractionextracted with EtOAc (3×10 mL)
  3. washThe combined organic layers were then washed with water (5 mL) and brine (5 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe resulted light yellow product was purified by flash column chromatography (silica gel, CH2Cl2/MeOH, 9:1)

Sources & evidence

ORD record
ord-4bc94d64b7844f288022d334516edd4f
Source dataset
uspto-grants-2015_11
Patent number
US09185909B2

Reaction notes

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