Ethyl chloroacetate → ethyl N-{(1S,2S)-2-[(tert-butoxycarbonyl)amino]cyclopentyl}glycinate
Reaction equation
[NH2:1][C@H:2]1[CH2:6][CH2:5][CH2:4][C@@H:3]1[NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]>C(#N)C>[C:10]([O:9][C:8]([NH:7][C@H:3]1[CH2:4][CH2:5][CH2:6][C@@H:2]1[NH:1][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[O:14])([CH3:11])([CH3:13])[CH3:12]Participants
5
Conditions
- Temperature
- 55 °C
Procedure
tert-Butyl [(1S,2S)-2-aminocyclopentyl]carbamate (900 mg, 4.49 mmol) (purchased from Sigma Aldrich) was taken up in acetonitrile (13 mL). Potassium carbonate (932 mg, 6.74 mmol) and ethyl chloroacetate (0.577 mL, 5.39 mmol) were added, and the resulting mixture was heated to 55° C. overnight. The resulting mixture was cooled to room temperature and concentrated under reduced pressure. The residue was taken up in EtOAc, washed with water and brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (0-100% EtOAc/hexanes) to afford ethyl N-{(1S,2S)-2-[(tert-butoxycarbonyl)amino]cyclopentyl}glycinate.
Workup
- temperatureThe resulting mixture was cooled to room temperature
- concentrationconcentrated under reduced pressure
- washwashed with water and brine
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe resulting residue was purified by silica gel chromatography (0-100% EtOAc/hexanes)
Sources & evidence
- ORD record
- ord-41d0893314554d898c79fe3261f72c7d
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08962611B2
Reaction notes
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