Methanol → HCID 10002596, compound

HRID 2085605Notes

Reaction equation

HRID 2085605 reaction equation
C([O:3][C:4](=[O:33])/[CH:5]=[C:6](/[CH:8]=[CH:9]/[C@@H:10]1[CH2:12][C@@:11]1([C:14]1[CH:15]=[C:16]([CH2:25][CH2:26][CH:27]([OH:32])[CH2:28][CH2:29][CH2:30][CH3:31])[C:17]2[O:21][CH2:20][C:19]([CH3:23])([CH3:22])[C:18]=2[CH:24]=1)[CH3:13])\[CH3:7])C.CO.O1CCCC1.[OH-].[Na+]>C(#N)C.O>[OH:32][CH:27]([CH2:28][CH2:29][CH2:30][CH3:31])[CH2:26][CH2:25][C:16]1[C:17]2[O:21][CH2:20][C:19]([CH3:23])([CH3:22])[C:18]=2[CH:24]=[C:14]([C@@:11]2([CH3:13])[CH2:12][C@H:10]2/[CH:9]=[CH:8]/[C:6](/[CH3:7])=[CH:5]/[C:4]([OH:33])=[O:3])[CH:15]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 10456658HCID 10456658, compound2×

Product 1

HCID 10002596HCID 10002596, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Following General Procedure H and using (E)-3-((E)-2-{(1S,2S)-2-[7-(3-hydroxy-heptyl)-3,3-dimethyl-2,3-dihydro-benzofuran-5-yl]-2-methyl-cyclopropyl}-vinyl)-but-2-enoic acid ethyl ester (Compound 37, 0.007 g, 0.015 mmol), methanol (1.5 mL), tetrahydrofuran (1.5 mL) and 1M aqueous sodium hydroxide (0.5 mL) followed by preparative reverse phase HPLC using 10% water in acetonitrile as the eluent, the title compound was obtained (0.0044 g, 67%).

Sources & evidence

ORD record
ord-00ac5212fd9a4c1fa62c712485bad0c5
Source dataset
uspto-grants-2004_04
Patent number
US06720423B2

Reaction notes

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