Hydrochloric Acid → HCID 86657900, compound
Reaction equation
[C:1]([O:5][C:6](=[O:12])[N:7]([CH2:9][CH2:10][OH:11])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[OH-].[K+].Br[CH2:16][CH2:17][F:18].Cl>C1(C)C=CC=CC=1.[N+](CCCC)(CCCC)(CCCC)CCCC.[O-]S(O)(=O)=O.CCOC(C)=O.CCCCCC.O>[C:1]([O:5][C:6](=[O:12])[N:7]([CH2:9][CH2:10][O:11][CH2:16][CH2:17][F:18])[CH3:8])([CH3:4])([CH3:2])[CH3:3]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 80 °C
Procedure
To a solution of (2-hydroxy-ethyl)-methyl-carbamic acid tert-butyl ester (CAS Nr. 57561-39-4; 2.50 g, 14.3 mmol) in toluene (35 ml) was added powered KOH (2.8 g, 50 mmol) and Bu4NHSO4 (0.97 mg, 2.86 mmol). The reaction mixture was stirred vigorously and heated to 50° C. while neat 1-bromo-2-fluoro-ethane (2.72 g, 21.4 mmol) was added slowly. The temperature was increased to 80° C. and maintained for 3-5 h. The reaction mixture was cooled to RT, water was added (50 ml) and the pH was adjusted to 7 with 1N HCl solution. Extraction with EtOAc (2×150 ml), washing with brine, drying with Na2SO4 and concentrating under vacuum yielded the crude product. The crude material was subjected to column chromatography on silica by EtOAc:hexane (10:90 to 20:80) to give the desired product as light yellow liquid (1.2 g, 38%). MS (m/z)=122.0 [M−Boc+]; 166.2 [M−tBu+].
Workup
- additionwas added slowly
- temperaturemaintained for 3-5 h
- temperatureThe reaction mixture was cooled to RT
- extractionExtraction with EtOAc (2×150 ml)
- washwashing with brine
- dry with materialdrying with Na2SO4
- concentrationconcentrating under vacuum
- customyielded the crude product
Sources & evidence
- ORD record
- ord-b85e88d6e81a43e0bae1443d39aba04c
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08410117B2
Reaction notes
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