Methanol → HCID 9929897, compound

HRID 2085581Notes

Reaction equation

HRID 2085581 reaction equation
C([O:3][C:4](=[O:30])/[CH:5]=[C:6](\[CH3:29])/[CH:7]=[CH:8]/[C@@H:9]1[CH2:11][C@@:10]1([C:13]1[CH:14]=[C:15]([CH2:24][C:25]([CH3:28])([CH3:27])[CH3:26])[C:16]2[O:20][CH2:19][C:18]([CH3:22])([CH3:21])[C:17]=2[CH:23]=1)[CH3:12])C.CO.[OH-].[Na+].C(OCC)(=O)C>CCCCCC.C(#N)C.O>[CH3:26][C:25]([CH3:28])([CH3:27])[CH2:24][C:15]1[C:16]2[O:20][CH2:19][C:18]([CH3:21])([CH3:22])[C:17]=2[CH:23]=[C:13]([C@@:10]2([CH3:12])[CH2:11][C@H:9]2/[CH:8]=[CH:7]/[C:6](/[CH3:29])=[CH:5]/[C:4]([OH:30])=[O:3])[CH:14]=1

Participants

8

Reactant 4

HCID 887MethanolHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 10093005HCID 10093005, compound2×

Product 1

HCID 9929897HCID 9929897, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8058HexaneSolvent

Procedure

Following General Procedure H and using 5-{(1S, 2S) 2-[7-(2,2-dimethyl-propyl)-3,3-dimethyl-2,3-dihydro-benzofuran-5-yl]-2-methyl-cyclopropyl}-3-methyl-penta-2E,4E-dienoic acid ethyl ester (Compound 11, 0.132 g, 0.32 mmol), 15 mL of methanol and 5M aqueous sodium hydroxide (2 mL) followed by flash column chromatography using 25% ethyl acetate in hexane as the eluent and preparative reverse phase HPLC using 12% water in acetonitrile as the mobile phase, the title compound was obtained (0.098 g, 75%) as a white solid.

Sources & evidence

ORD record
ord-bf072fcae9a047ef8a7533acb0eaacbe
Source dataset
uspto-grants-2004_04
Patent number
US06720423B2

Reaction notes

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