Sodium Hydroxide → HCID 11169884, compound

HRID 1353192Notes

Reaction equation

HRID 1353192 reaction equation
C([O:3][C:4](=[O:54])[C@@H:5]([O:51][CH2:52][CH3:53])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14]/[CH:15]=[C:16](/[C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][C:27](/[C:30](/[CH3:50])=[CH:31]/[CH2:32][O:33][C:34]4[CH:39]=[CH:38][C:37]([CH2:40][C@H:41]([O:47][CH2:48][CH3:49])[C:42]([O:44]CC)=[O:43])=[CH:36][CH:35]=4)=[CH:26][CH:25]=3)=[CH:20][CH:19]=2)\[CH3:17])=[CH:9][CH:8]=1)C.[OH-].[Na+]>C(O)C.O.C(OCC)(=O)C>[C:42]([C@@H:41]([O:47][CH2:48][CH3:49])[CH2:40][C:37]1[CH:36]=[CH:35][C:34]([O:33][CH2:32]/[CH:31]=[C:30](/[C:27]2[CH:28]=[CH:29][C:24]([C:21]3[CH:22]=[CH:23][C:18](/[C:16](/[CH3:17])=[CH:15]/[CH2:14][O:13][C:10]4[CH:9]=[CH:8][C:7]([CH2:6][C@H:5]([O:51][CH2:52][CH3:53])[C:4]([OH:54])=[O:3])=[CH:12][CH:11]=4)=[CH:19][CH:20]=3)=[CH:25][CH:26]=2)\[CH3:50])=[CH:39][CH:38]=1)([OH:44])=[O:43]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 11320149HCID 11320149, compound

Product 1

HCID 11169884HCID 11169884, compoundYield 53%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (E)(E)(S)(S) 2-ethoxy-3-{4-[3-(4′-{3-[4-(2-ethoxy-2-ethoxycarbonyl-ethyl)-phenoxy]-1-methyl-propenyl}-biphenyl-4-yl)-but-2-enyloxy]-phenyl}-propionic acid ethyl ester (example 11) (367 mg 0.5 mmol) in ethanol (10 mL) was added 1N sodium hydroxide (2 mL). The reaction mixture was stirred at room temperature for 18 h, and at 60° C. 1 h. The resulting mixture was diluted with water and ethyl acetate, the aqueous layer collected and further extracted with ethyl acetate (3×). The organic layers were combined, washed with brine, dried (MgSO4) and evaporated to give 180 mg (53%) of the title compound.

Workup

  1. customat 60° C
  2. custom1 h
  3. customthe aqueous layer collected
  4. extractionfurther extracted with ethyl acetate (3×)
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-f9deea2c1165444f9306c74893d1b100
Source dataset
uspto-grants-2007_05
Patent number
US07220877B2

Reaction notes

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