Sodium Hydroxide → HCID 86588428, compound

HRID 1353200Notes

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

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of (E)(E)(S)(S) 2-ethoxy-3-{4-[5-(3-{5-[4-(2-ethoxy-2-ethoxycarbonyl-ethyl)-phenoxy]-3-methyl-pent-3-en-1-ynyl}-phenyl)-3-methyl-pent-2-en-4-ynyloxy]-phenyl}-propionic acid ethyl ester (example 27) (255 mg 0.36 mmol) in ethanol (10 mL) was added 1N sodium hydroxide (3.6 mL). After stirring at 60° C. for 30 min, the reaction mixture was concentrated in vacuo and added 1N hydrochloride acid. The product was extracted with dichloromethane (×3). The combined organic phases were dried (MgSO4), filtered and concentrated in vacuo to give 232 mg (99%) of the title compound.

Workup

concentrationthe reaction mixture was concentrated in vacuo
additionadded 1N hydrochloride acid
extractionThe product was extracted with dichloromethane (×3)
dry with materialThe combined organic phases were dried (MgSO4)
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-4b78f21b9ed147738146c607a33d41cf
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07220877B2

Reaction notes

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