Ethyl Acetate → HCID 22237525, compound

HRID 1281409Notes

Reaction equation

HRID 1281409 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

6

Reactant 4

HCID 8857Ethyl AcetateHCID 13583DodecylamineHCID 54518874HCID 54518874, compoundHCID 178418339Butyllithium2×

Product 1

HCID 22237525HCID 22237525, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

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 min 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 was 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

  1. additionWhen the addition
  2. waitat room temperature for 30 min
  3. temperaturea cooled (0° C.) solution
  4. stirringThe reaction was stirred for 10 min at 0° C. when
  5. additionthe addition
  6. customat room temperature
  7. customovernight
  8. temperatureThen the reaction mixture was heated to 35° C. for 1 hour
  9. customThe reaction

Sources & evidence

ORD record
ord-b08fa387792443208be1eaa9b5d65818
Source dataset
uspto-grants-2002_09
Patent number
US06451827B2

Reaction notes

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