Methanol → HCID 66935020, compound
Reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C@@H:10]([CH2:14][C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=1[O:22][CH3:23])[C:11]([OH:13])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:24](C1NC=CN=1)(C1NC=CN=1)=O.CO.C(N(CC)CC)C>O1CCCC1.O>[C:1]([O:5][C:6]([NH:8][CH2:9][C@@H:10]([CH2:14][C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=1[O:22][CH3:23])[C:11]([O:13][CH3:24])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2]Participants
Procedure
To a solution of (2R)-3-[(tert-butoxycarbonyl)amino]-2-(5-chloro-2-methoxybenzyl)propionic acid (1.1 g, 98% ee) in tetrahydrofuran (32 ml), carbonyl diimidazole (600 mg) was added under ice cooling and the mixture was stirred at room temperature for 1 hour 20 minutes. To the reaction solution, methanol (12.5 ml) and triethylamine (4.3 ml) were added and the mixture was stirred at room temperature for 3 hours. To the reaction solution, water was added and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, then solvent was distilled off in vacuo. The obtained residue was purified by silica gel column chromatography to obtain the title compound (1.03 g, 98%ee) as an oily substance.
Workup
- stirringthe mixture was stirred at room temperature for 3 hours
- extractionthe mixture was extracted with ethyl acetate
- dry with materialThe organic layer was dried over anhydrous magnesium sulfate
- distillationsolvent was distilled off in vacuo
- customThe obtained residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-0465f7054c1e4e978386379d3d3f3b12
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08049006B2
Reaction notes
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