Hydrochloric Acid → HCID 73117393, compound

HRID 1182505Notes

Reaction equation

HRID 1182505 reaction equation
[OH:1][NH:2][C:3](=[O:29])[CH:4]=[CH:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]([O:21][Si](C(C)(C)C)(C)C)[C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=1.Cl.C(OCC)(=O)C.O>C1COCC1>[OH:1][NH:2][C:3](=[O:29])[CH:4]=[CH:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]([OH:21])[C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8857Ethyl AcetateHCID 85350900HCID 85350900, compound

Product 1

HCID 73117393HCID 73117393, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
30 °C

Procedure

To a solution of the silyl ether 186 (300 mg, 0.725 mmol) in THF (3 mL) at room temperature was added 1N aqueous solution of hydrochloric acid (3 mL). The mixture was stirred for 3 hours at 30° C. and then added a large volume of ethyl acetate and water. The water layer was washed with ethyl acetate and the combined organic layers were washed with brine, dried (MgSO4) and concentrated in vacuo. The crude residue was purified by flash chromatography (75% to 100% ethyl acetate/hexane) affording unsatisfactory purity. So the compound was purified again using 8% methanol in dichloromethane affording the title compound 187 in 33% yield (77 mg). 1H NMR: (300 MHz, CD3OD) δ: 7.87-7.71 (m, 4H), 7.52-7.40 (m, 3H), 6.77 (dt, J=15.1, 6.9 Hz, 1H), 5.75 (d, J=15.1 Hz, 1H), 4.76 (t, J=6.9 Hz, 1H), 2.17-2.10 (m, 2H), 1.84-1.77 (m, 2H), 1.49-1.27 (m, 4H) 1.88-1.75 (m, 4). MS (ESI)=282 (M+−OH), 322 (M++Na).

Workup

  1. washThe water layer was washed with ethyl acetate
  2. washthe combined organic layers were washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was purified by flash chromatography (75% to 100% ethyl acetate/hexane)
  6. customaffording unsatisfactory purity
  7. customSo the compound was purified again

Sources & evidence

ORD record
ord-c41e9f9978544f1b8dc7c284a9f86a9d
Source dataset
uspto-grants-2007_10
Patent number
US07288567B2

Reaction notes

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