Hexyl chloroformate → HCID 59924190, compound
Reaction equation
[OH:1][C@@H:2]([CH3:12])[C@H:3]([NH2:11])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([OH:10])[CH:5]=1.C(=O)(O)[O-].[Na+].Cl[C:19]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[O:20]>O1CCCC1.O1CCOCC1>[CH2:22]([O:21][C:19]([NH:11][C@H:3]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([OH:10])[CH:5]=1)[C@H:2]([CH3:12])[OH:1])=[O:20])[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a solution of (1R,2S)-2-hydroxy-1-(3-hydroxyphenyl)propylamine (17.2 g) in tetrahydrofuran (500 ml) was added 0.5M aqueous solution of sodium bicarbonate (500 ml) and the mixture was stirred at 0° C. To the mixture was added a solution of hexyl chloroformate (14 g) in dioxane (20 ml) and the mixture was stirred for 30 minutes at 0° C. The reaction mixture was extracted with ethyl acetate (300 ml). The organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and then concentrated. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=4:1→2:1→3:2) to give the title compound (24.2 g) having the following physical data.
Workup
- stirringthe mixture was stirred for 30 minutes at 0° C
- extractionThe reaction mixture was extracted with ethyl acetate (300 ml)
- washThe organic layer was washed with a saturated aqueous solution of sodium chloride
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated
- customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=4:1→2:1→3:2)
Sources & evidence
- ORD record
- ord-2326115b353d4211b98aed534628acb3
- Source dataset
- uspto-grants-2002_12
- Patent number
- US06495533B1
Reaction notes
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