Sodium Hydroxide → HCID 86588421, compound

HRID 1353198Notes

Reaction equation

HRID 1353198 reaction equation
[CH2:1]([O:3][C:4](=[O:52])[C@@H:5]([O:49][CH2:50][CH3:51])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14]/[CH:15]=[CH:16]/[C:17]#[C:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]#[C:26]/[CH:27]=[CH:28]/[CH2:29][O:30][C:31]3[CH:36]=[CH:35][C:34]([CH2:37][C@H:38]([O:44][CH2:45][CH3:46])[C:39]([O:41]CC)=[O:40])=[CH:33][C:32]=3[Br:47])=[CH:21][CH:20]=2)=[C:9]([Br:48])[CH:8]=1)[CH3:2].[OH-].[Na+]>C1COCC1.C(O)C>[Br:47][C:32]1[CH:33]=[C:34]([CH2:37][C@H:38]([O:44][CH2:45][CH3:46])[C:39]([OH:41])=[O:40])[CH:35]=[CH:36][C:31]=1[O:30][CH2:29]/[CH:28]=[CH:27]/[C:26]#[C:25][C:22]1[CH:21]=[CH:20][C:19]([C:18]#[C:17]/[CH:16]=[CH:15]/[CH2:14][O:13][C:10]2[CH:11]=[CH:12][C:7]([CH2:6][C@H:5]([O:49][CH2:50][CH3:51])[C:4]([O:3][CH2:1][CH3:2])=[O:52])=[CH:8][C:9]=2[Br:48])=[CH:24][CH:23]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86588420HCID 86588420, compound

Product 1

HCID 86588421HCID 86588421, compoundYield 94.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (E)(E)(S)(S) 3-{3-bromo-4-[5-(4-{5-[2-bromo-4-(2-ethoxy-2-ethoxycarbonyl-ethyl)-phenoxy]-pent-3-en-1-ynyl}-phenyl)-pent-2-en-4-ynyloxy]-phenyl}-2-ethoxy-propionic acid ethyl ester (example 19) (250 mg 0.30 mmol) in THF (2 mL) and ethanol (3 mL) was added 1N sodium hydroxide (3 mL). After stirring at room temperature for 1 h, the reaction mixture was concentrated in vacuo, added water and 1N hydrochloride acid to pH 1. The product was extracted with ethyl acetate (×3) and the combined organic phases were washed with water, dried (MgSO4), filtered and concentrated in vacuo to give 230 mg of the title compound.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. additionadded water and 1N hydrochloride acid to pH 1
  3. extractionThe product was extracted with ethyl acetate (×3)
  4. washthe combined organic phases were washed with water
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-876c8cc073614f9fa66f5c99b4b41fe7
Source dataset
uspto-grants-2007_05
Patent number
US07220877B2

Reaction notes

Loading…