Lawesson's reagent → HCID 86590450, compound

HRID 490214Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=O)[CH2:10][N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[CH2:13][C@@H:12]2[CH3:23])[CH:5]=[CH:6][CH:7]=1.COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:34]2)=CC=1>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[S:34])[CH2:10][N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[CH2:13][C@@H:12]2[CH3:23])[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 65 °C

Procedure

A solution of the product from Example 214 (200 mg, 0.62 mmol) in dry toluene (6 mL) was treated with 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulphide (Lawesson's reagent, 125 mg, 0.31 mmol) and heated at 65° C. for 1 hour. The mixture was allowed to cool to room temperature and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (elution with 75% hexanes:ethyl acetate) to provide 173 mg (82% yield) of the title compound as a yellow oil. 1H NMR (300 MHz, CDCl3) δ 1.17 (d, J=6.1 Hz, 3H) 2.39 (s, 3H) 2.75 (dd, J=12.4, 9.8 Hz, 1H) 2.81 (m, 1H) 2.96 (m, 2H) 3.26 (t, J=5.5 Hz, 1H) 3.56 (d, J=17.6 Hz, 1H) 3.88 (d, J=17.6 Hz, 1H) 4.04 (m, 2H) 6.67 (t, J=6.1 Hz, 1H) 6.69 (d, J=8.5 Hz, 1H) 7.08 (d, J=7.5 Hz, 1H) 7.30 (t, J=7.8 Hz, 1H) 7.52 (ddd, J=8.7, 7.0, 2.0 Hz, 1H) 7.67 (s, 1H) 7.74 (d, J=8.1 Hz, 1H) 8.22 (dd, J=4.9, 1.9 Hz, 1H) 11.25 (s, 1H); MS (DCI/NH3) m/e 341.2 (M+H)+.

Workup

temperatureto cool to room temperature
concentrationconcentrated under reduced pressure
customThe residue was purified by flash column chromatography on silica gel (elution with 75% hexanes:ethyl acetate)

Sources & evidence

ORD record: ord-0eea15cf84284443b5befb4927a0b322
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07528134B2

Reaction notes

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