Sodium Hydroxide → HCID 86745711, compound

HRID 373251Notes

Reaction equation

HRID 373251 reaction equation
C[O:2][C:3]([CH2:5][CH2:6][CH2:7]/[CH:8]=[C:9]1\[CH2:10][C@@H:11]2[C@H:15]([CH2:16]\1)[C@@H:14]([CH2:17][CH2:18][CH:19]([OH:26])[CH:20]([F:25])[CH2:21][CH2:22][CH2:23][CH3:24])[C@H:13]([O:27][CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][O:29]1)[CH2:12]2)=[O:4].[OH-].[Na+]>CO>[C:3]([CH2:5][CH2:6][CH2:7]/[CH:8]=[C:9]1\[CH2:10][C@@H:11]2[C@H:15]([CH2:16]\1)[C@@H:14]([CH2:17][CH2:18][CH:19]([OH:26])[CH:20]([F:25])[CH2:21][CH2:22][CH2:23][CH3:24])[C@H:13]([O:27][CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][O:29]1)[CH2:12]2)([OH:4])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86745709HCID 86745709, compound

Product 1

HCID 86745711HCID 86745711, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(1S,2R,3R,5S)-7(E)-(4-Methoxycarbonylbutylidene)-2-[4(RS)-fluoro-3(RS)-hydroxy-octyl ]-3-tetrahydropyranyloxybicyclo[3.3.0]octane (12) (0.185 g) was dissolved in methanol. To the solution, an aqueous solution of 1N sodium hydroxide (6.5 ml) was added. The mixture was stirred at room temperature for 4 hours. After a usual work-up a crude product (1S,2R,3R,5S)-7(E)-(4-carboxybutylidene)-2-[4(RS)fluoro-3(RS )-hydroxyoctyl]-3-tetrahydropyranyloxybicyclo[3.3.0]octane (13) was obtained. Yield: 0.184 g

Sources & evidence

ORD record
ord-f6277a19807642da8283fd01df2aca3c
Source dataset
uspto-grants-1992_11
Patent number
US05162370

Reaction notes

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