HCID 68315188, compound → HCID 67207996, compound

HRID 2202145Notes

Reaction equation

HRID 2202145 reaction equation
COC([C@@]12C(C)(C)[C@@H](CC1)C=C2[C:14]1[C:19]([O:20][CH3:21])=[CH:18][C:17]([C:22]([CH3:30])([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH3:23])=[CH:16][C:15]=1[O:31][CH3:32])=O.FC(F)(F)S(O[C:39]1[C@@H:40]2[C:45]([CH3:47])([CH3:46])[C@:43]([CH3:48])([CH:44]=1)[CH2:42][CH2:41]2)(=O)=O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:32][O:31][C:15]1[CH:16]=[C:17]([C:22]([CH3:23])([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH3:30])[CH:18]=[C:19]([O:20][CH3:21])[C:14]=1[C:39]1[C@@H:40]2[C:45]([CH3:47])([CH3:46])[C@@:43]([CH3:48])([CH2:42][CH2:41]2)[CH:44]=1

Participants

4

Reactant 2

HCID 68315188HCID 68315188, compoundHCID 86671524HCID 86671524, compound

Product 1

HCID 67207996HCID 67207996, compound

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

The title compound was prepared by the general procedure described for compound 11a (HU-911), using pinacol arylboronate 3 (mixed with 4-alkyl resorcinol dimethylether 1) 0.755 g, enol triflate 19a 0.17 g (0.598 mmol), Pd(PPh3)4 0.041 g (0.036 mmol) and t-BuNF 0.9 ml (0.9 mmol, 1M solution in THF). The product was purified by silica gel column chromatography (petroleum ether/ether) to give oil 0.185 g (78%), which solidified upon standing at −20° C. mp 33-34° C.; 1H NMR (300 MHz, CDCl3) δ ppm 6.50 (s, 2H), 5.79 (d, J=3.00 Hz, 1H), 3.76 (s, 6H), 2.60 (d, J=3.51, 1H), 1.81 (m, 1H), 1.64 (m, 1H), 1.60 (m, 1H), 1.55 (m, 2H), 1.31 (m, 1H), 1.28 (s, 6H), 1.17-1.25 (m, 8H), 1.08 (s, 3H), 0.99 (s, 3H), 0.86 (t, J=6.69 Hz, 3H), 0.81 (s, 3H). Exact mass calculated for C27H42O2 m/e 398.32. found 398.82. Anal. calcd. for C27H42O2: C, 81.35; H, 10.62. Found: C, 81.50; H, 10.71.

Workup

  1. customThe product was purified by silica gel column chromatography (petroleum ether/ether)

Sources & evidence

ORD record
ord-23ff22612a2b46c3a8e5e4d65f62a45c
Source dataset
uspto-grants-2016_06
Patent number
US09365534B2

Reaction notes

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