Trifluoroacetic acid → HCID 54099082, compound

HRID 2225829Notes

Reaction equation

HRID 2225829 reaction equation
[CH2:1]([O:3][C:4](=[O:41])[C:5](=[O:40])[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([C:19]2[CH:24]=[C:23]([C:25]([CH3:28])([CH3:27])[CH3:26])[C:22]([O:29]COCCOC)=[C:21]([C:36]([CH3:39])([CH3:38])[CH3:37])[CH:20]=2)=[O:18])=[CH:8][CH:7]=1)[CH3:2].FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>ClCCl>[CH2:1]([O:3][C:4](=[O:41])[C:5](=[O:40])[C:6]1[CH:7]=[CH:8][C:9]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([C:19]2[CH:24]=[C:23]([C:25]([CH3:26])([CH3:27])[CH3:28])[C:22]([OH:29])=[C:21]([C:36]([CH3:39])([CH3:38])[CH3:37])[CH:20]=2)=[O:18])=[CH:10][CH:11]=1)[CH3:2]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 54161734HCID 54161734, compound

Product 1

HCID 54099082HCID 54099082, compoundYield 78.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Hydroxy-alpha-oxobenzeneacetic acid ethyl ester (1.44 g) and 55% sodium hydride (0.36 g) in dimethylformamide (30 mL) was stirred for 20 minutes and then treated with 5-bromo-1-[3,5-bis(1,1-dimethylethyl)-4-[(2-methoxyethoxy) methoxy]phenyl]pentanone (3.4 g) in dimethylformamide (6 mL). The mixture was stirred at room temperature for 20 hours and then after an additional 4 hours at 50° C., it was worked up as in Example 20. The residual oil was purified by HPLC (ethyl acetate-toluene; 1:17) to give 2.7 g of 4-[5-[3,5-bis(1,1-dimethylethyl)-4-[(2-methoxyethoxy) methoxy]phenyl]-5-oxopentyloxy]-alpha-oxobenzeneacetic acid ethyl ester as an oil. A solution of the above 4-[5-[3,5-bis(1,1-dimethylethyl)-4-[(2-methoxyethoxy) methoxy]phenyl]-5-oxopentyloxy]-alpha-oxobenzeneacetic acid ethyl ester (2.1 g) was dissolved in dichloromethane (20 mL) containing trifluoroacetic acid (1.1 mL) was stirred at room temperature for 31 hours, then saturated sodium bicarbonate solution was added (25 mL). The separated organic layer was dried (MgSO4) and evaporated and the crude product was purified by HPLC (ethyl acetate-hexane; 4:21). Trituration of the resulting material with hexane afforded 1.4 g of 4-[5-[3,5-bis(1,1-dimethylethyl) -4-hydroxyphenyl]-5-oxopentyloxy]-alpha-oxobenzeneacetic acid ethyl ester, mp 95°-96° C.

Workup

  1. dry with materialThe separated organic layer was dried (MgSO4)
  2. customevaporated
  3. customthe crude product was purified by HPLC (ethyl acetate-hexane; 4:21)

Sources & evidence

ORD record
ord-ebdd3d688d634df782c85e8d1dc35796
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

Loading…