Triphosgene → HCID 59571236, compound
Reaction equation
[Cl-].[CH2:2]([O:4][C:5](=[O:15])[C@@H:6]([NH3+:14])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[CH3:3].[C:16]([O-])(O)=[O:17].[Na+].ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[N:14]([C@@H:6]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]=[CH2:13])[C:5]([O:4][CH2:2][CH3:3])=[O:15])=[C:16]=[O:17]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of (2S)-1-ethoxy-1-oxononan-2-aminium chloride (4.00 g, 16.97 mmol) and DCM (80 ml) was cooled to 0° C. A solution of saturated NaHCO3 (80.0 ml, 84 mmol) was added, and then triphosgene (1.662 g, 5.60 mmol) was added. The reaction mixture was stirred at 0° C. for 1 hour, and then the layers were separated. The aqueous layer was extracted with DCM (3×). The combined organic portions were washed with brine, dried with MgSO4 and filtered and concentrated. The crude product was subjected to silica gel chromatography (80:20 hexane/EtOAc) to give the title compound.
Workup
- customthe layers were separated
- extractionThe aqueous layer was extracted with DCM (3×)
- washThe combined organic portions were washed with brine
- dry with materialdried with MgSO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-36eb353fb0eb4e16bffd4792076da81c
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08377874B2
Reaction notes
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