Sodium Hydroxide → HCID 10371709, compound

HRID 1353183Notes

Reaction equation

HRID 1353183 reaction equation
C([O:3][C:4](=[O:50])[C@@H:5]([O:47][CH2:48][CH3:49])[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][CH:32]=3)=[CH:21][CH:20]=2)=[CH:9][CH:8]=1)C.[OH-].[Na+]>C1COCC1.C(O)C>[C:39]([C@@H:38]([O:44][CH2:45][CH3:46])[CH2:37][C:34]1[CH:33]=[CH:32][C:31]([O:30][CH2:29]/[CH:28]=[CH:27]/[C:26]#[C:25][C:22]2[CH:23]=[CH:24][C:19]([C:18]#[C:17]/[CH:16]=[CH:15]/[CH2:14][O:13][C:10]3[CH:9]=[CH:8][C:7]([CH2:6][C@H:5]([O:47][CH2:48][CH3:49])[C:4]([OH:50])=[O:3])=[CH:12][CH:11]=3)=[CH:20][CH:21]=2)=[CH:36][CH:35]=1)([OH:41])=[O:40]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86588409HCID 86588409, compound

Product 1

HCID 10371709HCID 10371709, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (E)(E)(S)(S) 2-ethoxy-3-{4-[5-(4-{5-[4-(2-ethoxy-2-ethoxycarbonyl-ethyl)-phenoxy]-pent-3-en-1-ynyl}-phenyl)-pent-2-en-4-ynyloxy]-phenyl}-propionic acid ethyl ester (example 1) (88 mg 0.13 mmol) in THF (3 mL) and ethanol (3 mL) was added 1N sodium hydroxide (2 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 dichloromethane (×3) and the combined organic phases were dried (MgSO4), filtered and concentrated in vacuo to give the title compound as a crystalline product. The product was recrystallised from ethyl acetate and petroleum ether to give 35 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 dichloromethane (×3)
  4. dry with materialthe combined organic phases were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fd474726acd24979bae06bf64bd23c49
Source dataset
uspto-grants-2007_05
Patent number
US07220877B2

Reaction notes

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