Sodium Hydroxide → HCID 86588419, compound

HRID 1353194Notes

Reaction equation

HRID 1353194 reaction equation
C([O:3][C:4](=[O:60])[C@@H:5]([O:57][CH2:58][CH3:59])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14]/[CH:15]=[C:16](\[CH3:56])/[C:17]#[C:18][C:19]2[CH:31]=[CH:30][C:29]3[C:28]4[C:23](=[CH:24][C:25]([C:32]#[C:33]/[C:34](/[CH3:54])=[CH:35]/[CH2:36][O:37][C:38]5[CH:43]=[CH:42][C:41]([CH2:44][C@H:45]([O:51][CH2:52][CH3:53])[C:46]([O:48]CC)=[O:47])=[CH:40][CH:39]=5)=[CH:26][CH:27]=4)[C:22](=[O:55])[C:21]=3[CH:20]=2)=[CH:9][CH:8]=1)C.[OH-].[Na+]>C(O)C>[C:46]([C@@H:45]([O:51][CH2:52][CH3:53])[CH2:44][C:41]1[CH:40]=[CH:39][C:38]([O:37][CH2:36]/[CH:35]=[C:34](\[CH3:54])/[C:33]#[C:32][C:25]2[CH:24]=[C:23]3[C:28]([C:29]4[CH:30]=[CH:31][C:19]([C:18]#[C:17]/[C:16](/[CH3:56])=[CH:15]/[CH2:14][O:13][C:10]5[CH:9]=[CH:8][C:7]([CH2:6][C@H:5]([O:57][CH2:58][CH3:59])[C:4]([OH:60])=[O:3])=[CH:12][CH:11]=5)=[CH:20][C:21]=4[C:22]3=[O:55])=[CH:27][CH:26]=2)=[CH:43][CH:42]=1)([OH:48])=[O:47]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86588417HCID 86588417, compound

Product 1

HCID 86588419HCID 86588419, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (E)(E)(S)(S) 2-ethoxy-3-{4-[5-(7-{5-[4-(2-ethoxy-2-ethoxycarbonyl-ethyl)-phenoxy]-3-methyl-pent-3-en-1-ynyl}-9-oxo-9H-fluoren-2-yl)-3-methyl-pent-2-en-4-ynyloxy]-phenyl}-propionic acid ethyl ester (example 13) (185 mg, 0.23 mmol) in ethanol (10 mL) was added 1N sodium hydroxide (2.3 mL). After stirring at 60° C. for 30 min., 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 160 mg of the title compound as a crystalline product.

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-f8ca283b84e44502b76f2ad4368c3a96
Source dataset
uspto-grants-2007_05
Patent number
US07220877B2

Reaction notes

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