Hydrochloric Acid → HCID 57586441, compound

HRID 420407Notes

Reaction equation

HRID 420407 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:17])[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([N:14]([CH3:16])[CH3:15])=[CH:10][CH:9]=2)[CH:7]=1.C([O:20][C:21](=[O:46])[CH2:22][CH2:23][CH2:24][O:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]Br)[C:27]=1[CH2:39][CH2:40][C:41]([O:43]CC)=[O:42])C.C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+].Cl>O.CC(N(C)C)=O>[Br:1][C:2]1[CH:3]=[C:4]([O:17][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][C:28]2[C:27]([CH2:39][CH2:40][C:41]([OH:43])=[O:42])=[C:26]([CH:31]=[CH:30][CH:29]=2)[O:25][CH2:24][CH2:23][CH2:22][C:21]([OH:46])=[O:20])[CH:5]=[C:6]([C:8]2[CH:9]=[CH:10][C:11]([N:14]([CH3:15])[CH3:16])=[CH:12][CH:13]=2)[CH:7]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 575864914-[3-(6-Bromo-hexyl)-2-(ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl esterHCID 57586502HCID 57586502, compound

Product 1

HCID 57586441HCID 57586441, compoundYield 42.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
90 °C

Procedure

In a round bottom vial charged with 100 mg (0.342 mmol) of 5-bromo-4′-dimethylamino-biphenyl-3-ol, 160 mg (0.342 mmol) of 4-[3-(6-bromo-hexyl)-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester, potassium carbonate (94 mg, 0.684 mmol) and 10 mL of DMA were sequentially added. This mixture was heated overnight at 90° C. HPLC analysis of the reaction mixture at this time, indicated the formation of the di-ester intermediate. At this time, 1 mL of 1 N NaOH aq. was added and the reaction mixture was heated again at 90° C. overnight. At this time, the reaction was diluted with water and acidified with 2 N HCl until pH=˜7 was achieved. The aqueous phase was thrice extracted with ethyl acetate. The combined organic phases were dried with MgSO4, filtered and washed with ethyl acetate. The filtrate was concentrated in vacuo to provide an oil (91 mg, 42%). This intermediate was used in subsequent steps without further purification.

Workup

  1. additionwere sequentially added
  2. temperaturethe reaction mixture was heated again at 90° C. overnight
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic phases were dried with MgSO4
  5. filtrationfiltered
  6. washwashed with ethyl acetate
  7. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-90e0e2a7e784430bae1dcf0cc76caf9f
Source dataset
uspto-grants-2012_01
Patent number
US08093385B2

Reaction notes

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