Hydrochloric Acid → HCID 57551975, compound
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([OH:13])[C@H:10]2[O:14][CH2:15][C:16]([O:19][CH3:20])([O:17][CH3:18])[C@@H:9]12)=[O:7])([CH3:4])(C)C.Cl.N1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(Cl)(OCC1C=CC=CC=1)=O>C(Cl)Cl.CO>[CH2:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([OH:13])[C@H:10]2[O:14][CH2:15][C:16]([O:17][CH3:18])([O:19][CH3:20])[C@@H:9]12)=[O:7])[C:4]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1Participants
7
Conditions
- Temperature
- 0 °C
Procedure
To a stirred solution of compound 12c (3.8 g, 13.13 mmol) in CH2Cl2 (100 mL) was added 2M HCl in MeOH (50 mL). The resulting solution was stirred overnight and then concentrated in vacuo and azeotroped with toluene (3×100 mL). The crude residue was dissolved in CH2Cl2 (100 mL) cooled to 0° C. and pyridine (1071 μL, 13.13 mmol) added followed by dropwise addition of CbzCl (1875 μL, 13.13 mmol). The reaction was stirred at room temperature for 2 hours then washed with 2 M HCl (2×50 mL), saturated NaHCO3 (2×50 mL), dried (MgSO4) and concentrated. The residue was purified by flash column chromatography (5-100% isohexane:EtOAc) to obtain the title compound as a clear oil (2510 mg, 59%). MS M+H 324.
Workup
- concentrationconcentrated in vacuo
- customazeotroped with toluene (3×100 mL)
- dissolutionThe crude residue was dissolved in CH2Cl2 (100 mL)
- stirringThe reaction was stirred at room temperature for 2 hours
- washthen washed with 2 M HCl (2×50 mL), saturated NaHCO3 (2×50 mL)
- dry with materialdried (MgSO4)
- concentrationconcentrated
- customThe residue was purified by flash column chromatography (5-100% isohexane:EtOAc)
Sources & evidence
- ORD record
- ord-11815764c85345dfa658a768021e4d35
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08466158B2
Reaction notes
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