HCID 117653526, compound → HCID 117653620, compound

HRID 1486518Notes

Reaction equation

HRID 1486518 reaction equation
C(O[C:4](=[O:31])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([C:18]2[CH:28]=[CH:27][C:21]([O:22][CH2:23][C:24]([OH:26])=[O:25])=[C:20]([CH3:29])[CH:19]=2)([CH2:16][CH3:17])[CH2:14][CH3:15])=[CH:9][C:8]=1[CH3:30])C.[CH3:32][CH2:33][Mg+].[Br-].O[C:37](C)(C)[CH2:38]OC1C=CC(C(C2C=CC(OCC(O)=O)=C(C)C=2)(CC)CC)=CC=1C>CCOCC>[CH2:37]([C:4]([OH:31])([CH2:33][CH3:32])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([C:18]2[CH:28]=[CH:27][C:21]([O:22][CH2:23][C:24]([OH:26])=[O:25])=[C:20]([CH3:29])[CH:19]=2)([CH2:16][CH3:17])[CH2:14][CH3:15])=[CH:9][C:8]=1[CH3:30])[CH3:38]

Participants

5

Reactant 3

HCID 117653526HCID 117653526, compoundHCID 117653645HCID 117653645, compoundHCID 178461630HCID 178461630, compound

Product 1

HCID 117653620HCID 117653620, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The title compound 13 was prepared from compound 4 (91.2 mg, 0.2128 mmol) and EtMgBr (227 μL of a 3.0 M solution in Et2O, 0.681 mmol, 3.2 equiv.) following the same procedure as that for compound 12. Purification by column chromatography (1:10:90→2:15:85 AcOH/EtOAc/CH2Cl2) afforded the title compound 13 (55.2 mg, 59%)

Workup

  1. customPurification by column chromatography (1:10:90→2:15:85 AcOH/EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-af9d0ad5a4bb455da21d837fcc28dfbc
Source dataset
uspto-grants-2016_08
Patent number
US09428447B2

Reaction notes

Loading…