Hydrochloric Acid → HCID 21102447, compound

HRID 1353196Notes

Reaction equation

HRID 1353196 reaction equation
[CH3:1][O:2][C:3](=[O:44])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13]/[CH:14]=[CH:15]/[C:16]#[C:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]#[C:25]/[CH:26]=[CH:27]/[CH2:28][O:29][C:30]3[CH:35]=[CH:34][C:33]([O:36][CH2:37][C:38]([O:40]C)=[O:39])=[C:32]([CH3:42])[CH:31]=3)=[CH:20][CH:19]=2)=[CH:8][C:7]=1[CH3:43].[OH-].[Na+].O.Cl>C(O)C.C1COCC1>[CH3:1][O:2][C:3]([CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13]/[CH:14]=[CH:15]/[C:16]#[C:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]#[C:25]/[CH:26]=[CH:27]/[CH2:28][O:29][C:30]3[CH:35]=[CH:34][C:33]([O:36][CH2:37][C:38]([OH:40])=[O:39])=[C:32]([CH3:42])[CH:31]=3)=[CH:20][CH:19]=2)=[CH:8][C:7]=1[CH3:43])=[O:44]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 58864666HCID 58864666, compound

Product 1

HCID 21102447HCID 21102447, compoundYield 68.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (E)(E) [4-(5-{4-[5-(4-methoxycarbonylmethoxy-3-methyl-phenoxy)-pent-3-en-1-ynyl]-phenyl}-pent-2-en-4-ynyloxy)-2-methyl-phenoxy]-acetic acid methyl ester (example 17) (15 mg, 0.025 mmol) in ethanol (15 mL) and THF (5 mL) was added 1N sodium hydroxide (1.0 mL). After stirring at room temperature for 30 min., the reaction mixture was 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 10 mg of the title compound.

Workup

  1. extractionThe product was extracted with dichloromethane (×3)
  2. dry with materialthe combined organic phases were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-58889d9133e34231bba1a3d8af3d328c
Source dataset
uspto-grants-2007_05
Patent number
US07220877B2

Reaction notes

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