Dimethylamine → HCID 67338116, compound

HRID 1670118Notes

Reaction equation

HRID 1670118 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH2:25][CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[C:19]=2[CH2:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH:10]=1)[C:5](O)=[O:6].F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)[N:49]1[CH2:53]CC[CH2:50]1.CNC.C1COCC1.CCN(C(C)C)C(C)C>ClCCl.O>[CH2:31]([O:30][C:28](=[O:29])[CH2:27][CH2:26][CH2:25][O:24][C:20]1[CH:21]=[CH:22][CH:23]=[C:18]([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][O:11][C:9]2[CH:8]=[C:4]([C:5](=[O:6])[N:49]([CH3:53])[CH3:50])[CH:3]=[C:2]([Br:1])[CH:10]=2)[C:19]=1[CH2:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH3:32]

Participants

8

Reactant 5

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 67340836HCID 67340836, compound

Product 1

HCID 67338116HCID 67338116, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-bromo-5-{6-[2-(2-ethoxycarbonyl-ethyl)-3-(3-ethoxycarbonyl-propoxy)-phenyl]-hexyloxy}-benzoic acid (808 mg, 1.33 mmol), bromotripyrrolidinophosphonium hexafluorophosphate (PyBroP) (745 mg, 1.6 mmol) in dichloromethane (15 mL) were added dimethylamine in THF (800 μL, 1.6 mmol, 2 M solution) and DIPEA (463 μL, 2.66 mmol) at room temperature. The resulting clear solution was stirred for 36 h. Then, the reaction mixture was diluted with water (100 mL) and dichloromethane (50 mL). The two layers were separated and the aqueous layer was extracted with dichloromethane (50 mL). The combined organic extracts were washed with brine solution (200 mL) and dried over anhydrous magnesium sulfate. Filtration of the drying agent and concentration of the filtrate in vacuo gave the crude product which was purified by using an ISCO™ (40 g) column chromatography eluting with 40-60% ethyl acetate in hexanes to afford 4-{3-[6-(3-bromo-5-dimethylcarbamoyl-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy}-butyric acid ethyl ester (757 mg, 90%) as a colorless oil

Workup

  1. customThe two layers were separated
  2. extractionthe aqueous layer was extracted with dichloromethane (50 mL)
  3. washThe combined organic extracts were washed with brine solution (200 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationFiltration of the drying agent and concentration of the filtrate in vacuo
  6. customgave the crude product which
  7. customwas purified
  8. washeluting with 40-60% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-70e1d38d6f754ba491611299ab959475
Source dataset
uspto-grants-2011_08
Patent number
US07989454B2

Reaction notes

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