HCID 68315186, compound → HCID 67207079, compound

HRID 2202141Notes

Reaction equation

HRID 2202141 reaction equation
[CH3:1][O:2][C:3]([C@@:5]12[C:11]([CH3:13])([CH3:12])[C@@H:8]([CH2:9][CH2:10]1)[CH:7]=[C:6]2[C:14]1[C:19]([O:20][CH3:21])=[CH:18][C:17]([C:22](C)([CH2:24][CH2:25][CH2:26][CH2:27]CC)C)=[CH:16][C:15]=1[O:31][CH3:32])=[O:4].COC1C=C(CCCCC)C=C(OC)C=1B1OC(C)(C)C(C)(C)O1.COC([C@@]12C(C)(C)[C@@H](CC1)C=C2OS(C(F)(F)F)(=O)=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>[CH3:1][O:2][C:3]([C@@:5]12[C:11]([CH3:12])([CH3:13])[C@@H:8]([CH2:9][CH2:10]1)[CH:7]=[C:6]2[C:14]1[C:15]([O:31][CH3:32])=[CH:16][C:17]([CH2:22][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:18][C:19]=1[O:20][CH3:21])=[O:4]

Participants

5

Reactant 3

HCID 68315186HCID 68315186, compoundHCID 68315188HCID 68315188, compoundHCID 86671523HCID 86671523, compound

Product 1

HCID 67207079HCID 67207079, 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 4 (mixed with 2) 0.244 g, enol triflate 9a 0.2 g (0.61 mmol), Pd(PPh3)4 0.042 g (0.037 mmol) and t-BuNF 0.91 ml (0.91 mmol, 1M solution in THF) to give colorless oil 170 mg (72%). 1H NMR (300 MHz, CDCl3) δ ppm 6.33 (s, 2H), 6.26 (d, J=3.42 Hz, 1H), 3.71 (s, 6H), 3.47 (s, 3H), 2.55 (t, J=7.70 Hz, 2H), 2.38-2.46 (m, 2H), 1.81-2.03 (m, 2H), 1.56-1.66 (m, 2H), 1.30-1.35 (m, 4H), 1.12 (s, 3H, syn), 1.07-1.16 (m, 1H), 0.97 (s, 3H, anti), 0.90 (t, J=6.84 Hz, 3H). Exact mass calculated for C24H34O4 by the general procedure described for compo4O4: C, 74.58; H, 8.87. Found: C, 74.61; H, 9.04.

Sources & evidence

ORD record
ord-e7259cf2e5364460b60fa69f5dff678f
Source dataset
uspto-grants-2016_06
Patent number
US09365534B2

Reaction notes

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