Sodium hydride → 2-(3,3''-Dichloro-5'-dodecylcarbamoyl-[1,1';3',1'']terphenyl-2'-yloxy-ethoxy]-acetic acid methyl ester

HRID 1743421Notes

Reaction equation

HRID 1743421 reaction equation
[CH2:1]([NH:13][C:14](=[O:39])[C:15]1[CH:20]=[C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=2)[C:18]([O:28][CH2:29][CH2:30][OH:31])=[C:17]([C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([Cl:38])[CH:33]=2)[CH:16]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[H-].[Na+].Br[CH2:43][C:44]([O:46][CH3:47])=[O:45]>C1COCC1>[CH3:47][O:46][C:44](=[O:45])[CH2:43][O:31][CH2:30][CH2:29][O:28][C:18]1[C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=2)=[CH:20][C:15]([C:14](=[O:39])[NH:13][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[CH:16][C:17]=1[C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([Cl:38])[CH:33]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 22237440N-Dodecyl-3,5-bis(3-chlorophenyl)-4-(2-hydroxyethoxy)benzamide

Product 1

HCID 867599412-(3,3''-Dichloro-5'-dodecylcarbamoyl-[1,1';3',1'']terphenyl-2'-yloxy-ethoxy]-acetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of N-dodecyl-3,5-bis(3-chlorophenyl)-4-(2-hydroxyethoxy)benzamide (Example 1, Step 2), (0.866 g, 1.52 mmol) in THF (8 mL) was added NaH (0.10 g, 80%, 3.34 mmol). The mixture was stirred at 60° C. for 50 min and was then cooled to room temperature. Methyl bromoacetate (0.158 mL, 2.67 mmol) was added and the mixture was stirred at 60° C. overnight. The reaction was cooled, quenched with 1.0 N HCl, and extracted with ethyl acetate. The organic phase was dried (MgSO4) and concentrated. Crude product was purified by HPLC. Yield: 0.177 g (18%) of product as an oil. 1H NMR (CDCl2) δ 7.72 (s, 2H), 7.63 (s, 2H), 7.50 (m, 2H), 7.39 (m, 4H), 6.20 (t, 1H), 3.78 (m, 5H), 3.49 (m, 4H), 3.31 (m, 2H), 1.68 (m, 2H), 1.30 (m, 18H), 0.88 (t, 3H).

Workup

  1. temperaturewas then cooled to room temperature
  2. stirringthe mixture was stirred at 60° C. overnight
  3. temperatureThe reaction was cooled
  4. customquenched with 1.0 N HCl
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic phase was dried (MgSO4)
  7. concentrationconcentrated
  8. customCrude product was purified by HPLC

Sources & evidence

ORD record
ord-062f3ad6d188461eb38f68ff59bfe714
Source dataset
uspto-grants-2006_03
Patent number
US07008636B2

Reaction notes

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