Ethyl Acetate → HCID 22237525, compound
Reaction equation
[CH2:1]([NH2:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[Li]CCCC.C([O:21][C:22]([C:24]1[CH:25]=[C:26]([C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([Cl:41])[CH:36]=2)[C:27]([O:31][CH2:32][CH2:33][OH:34])=[C:28]([Br:30])[CH:29]=1)=O)C.CCOC(C)=O>C1COCC1>[CH2:1]([NH:13][C:22]([C:24]1[CH:25]=[C:26]([C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([Cl:41])[CH:36]=2)[C:27]([O:31][CH2:32][CH2:33][OH:34])=[C:28]([Br:30])[CH:29]=1)=[O:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a cooled (0° C.) solution of dodecyl amine (3.22 g, 17.64 mmol) in 50 mL anhydrous THF was added n-BuLi (7.05 mL, 17.64 mmol) dropwise. When the addition was complete, the mixture was stirred for 10 mm at 0° C. then at room temperature for 30 min. This lithiated amine was added dropwise to a cooled (0° C.) solution of 5-bromo-3′-chloro-6-(2-hydroxy-ethoxy)-biphenyl-3-carboxylic acid ethyl ester (2.5 g, 5.78 mmol) in 40 mL anhydrous THF via cannula. The reaction was stirred for 10 min at 0° C. when the addition wag complete then at room temperature overnight. Then the reaction mixture was heated to 35° C. for 1 hour then more n-BuLi was added (0.7 mL, 1.75 mmol). The reaction was then worked up as in Step 2 of Example 135. There yielded 2.5 g, 80% of a yellow oil as desired product after flash chromatography (25% EtOAc:75% Hexanes) on silica gel.
Workup
- additionWhen the addition
- stirringThe reaction was stirred for 10 min at 0° C. when the addition wag complete
- customat room temperature
- customovernight
- temperatureThen the reaction mixture was heated to 35° C. for 1 hour
Sources & evidence
- ORD record
- ord-8ed0d98fefce4fe6a03a12b65f0d958b
- Source dataset
- uspto-grants-2001_04
- Patent number
- US06214877B1
Reaction notes
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