Acetic Acid → HCID 58392737, compound
Reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[N:30]=[CH:29][C@:28]2([C:31](=[O:34])[CH2:32][OH:33])[C@H:7]1[CH2:8][C@H:9]1[C@H:22]3[C@@:13]([F:26])([C@:14]4([CH3:25])[C:19]([C@@H:20]([F:23])[CH2:21]3)=[CH:18][C:17](=[O:24])[CH:16]=[CH:15]4)[C@@H:12]([OH:27])[CH2:11][C@@:10]12[CH3:35])=[O:5])[CH3:2].[BH3-]C#N.[Na+].C(O)(=O)C.C([O-])(O)=O.[Na+]>CO.[Cl-].[Na+].O>[CH2:1]([O:3][C:4]([CH:6]1[NH:30][CH2:29][C@:28]2([C:31](=[O:34])[CH2:32][OH:33])[C@H:7]1[CH2:8][C@H:9]1[C@H:22]3[C@@:13]([F:26])([C@:14]4([CH3:25])[C:19]([C@@H:20]([F:23])[CH2:21]3)=[CH:18][C:17](=[O:24])[CH:16]=[CH:15]4)[C@@H:12]([OH:27])[CH2:11][C@@:10]12[CH3:35])=[O:5])[CH3:2]Participants
7
Conditions
- Temperature
- 0 °C
Procedure
To a solution of intermediate 118 (629 mg; 1.28 mmol) in methanol (13 ml; 0.1 M), NaCNBH3 (169 mg; 2.56 mmol) is added at 0° C.; pH is adjusted to 5 by addition of acetic acid. The reaction mixture is stirred at 0° C. for 2 hours and at RT for 5 hours, then it is poured into brine (50 ml), and pH is adjusted to 7 by addition of a saturated solution of NaHCO3. The aqueous phase is extracted with AcOEt (3×60 ml) and the combined organic layers are concentrated. The crude material is purified by silica gel flash chromatography in gradient elution from DCM to DCM/MeOH 88:12, to afford pure title compound (335 mg, 53% yield mixture of stereoisomers).
Workup
- extractionThe aqueous phase is extracted with AcOEt (3×60 ml)
- concentrationthe combined organic layers are concentrated
- customThe crude material is purified by silica gel flash chromatography in gradient elution from DCM to DCM/MeOH 88:12
Sources & evidence
- ORD record
- ord-13f6acefcce24c31a8e1e25577a1cc77
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08481517B2
Reaction notes
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