Hydrochloric Acid → HCID 383045, compound
Reaction equation
COC[O:4][C:5]1[C:22]([O:23][CH2:24][CH3:25])=[CH:21][C@H:20]2[C:7](=[CH:8][CH2:9][C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[O:26]COC)[CH:6]=1.Cl>C1COCC1.[Cl-].[Na+].O>[CH2:24]([O:23][C:22]1[C:5]([OH:4])=[CH:6][C:7]2[CH2:8][CH2:9][C@@H:10]3[C@@H:19]([C:20]=2[CH:21]=1)[CH2:18][CH2:17][C@@:15]1([CH3:16])[C@H:11]3[CH2:12][CH2:13][C@@H:14]1[OH:26])[CH3:25]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 2 (6.0 g, 14.8 mmol) in THF (100 ml) was added 6 N HCl (100 ml) at room temperature and the resulting solution was stirred at room temperature for 6 hr. The reaction mixture was poured into brine (200 ml) and the products were extracted with ethyl acetate (3×100 ml). The ethyl acetate layers were washed with saturated sodium bicarbonate (100 ml) and brine (100 ml), combined and dried over sodium sulfate, and evaporated to dryness. Chromatography of the residue (silica gel 230-400 mesh, methylene chloride:ethyl acetate 9:1 by volume) gave compound 3 (4.04 g, 85%), which was crystallized from ethyl acetate/hexane to afford white crystals: mp 151-150° C. (lit.4 mp 154-155° C.); 1H NMR (CDCl3) δ6.95 (s, 1 H), 6.65 (s, 1 H), 4.08 (qd, J=6.8 Hz, J=1.5 Hz, 2 H), 3.73 (t, J=8.4 Hz, 1 H), 2.73 (m, 2 H), 2.30-1.20 (m, 18 H), 0.81 (s,3 H).
Workup
- extractionthe products were extracted with ethyl acetate (3×100 ml)
- washThe ethyl acetate layers were washed with saturated sodium bicarbonate (100 ml) and brine (100 ml)
- dry with materialdried over sodium sulfate
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-d32cb649cbf24c09b5d2bd9e07c29d6b
- Source dataset
- uspto-grants-2004_02
- Patent number
- US06696436B1
Reaction notes
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