Lawesson's reagent → HCID 25068634, compound

HRID 1879079Notes

Reaction equation

[CH3:1][C:2]([CH3:46])([CH2:44][CH3:45])[C:3]([O:5][CH:6]1[CH:15]2[C:10]([CH:11]=[CH:12][CH:13]([CH3:42])[CH:14]2[CH2:16][CH2:17][CH:18]2[CH2:23][CH:22]([O:24][C:25](=[O:40])[CH2:26][CH2:27][C:28]([O:30][C:31]3[CH:36]=[CH:35][C:34]([C:37](=O)[NH2:38])=[CH:33][CH:32]=3)=[O:29])[CH2:21][C:20](=[O:41])[O:19]2)=[CH:9][CH:8]([CH3:43])[CH2:7]1)=[O:4].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:56])=CC=1>C1C=CC=CC=1>[C:37]([C:34]1[CH:35]=[CH:36][C:31]([O:30][C:28](=[O:29])[CH2:27][CH2:26][C:25]([O:24][CH:22]2[CH2:21][C:20](=[O:41])[O:19][CH:18]([CH2:17][CH2:16][CH:14]3[CH:15]4[C:10](=[CH:9][CH:8]([CH3:43])[CH2:7][CH:6]4[O:5][C:3](=[O:4])[C:2]([CH3:1])([CH3:46])[CH2:44][CH3:45])[CH:11]=[CH:12][CH:13]3[CH3:42])[CH2:23]2)=[O:40])=[CH:32][CH:33]=1)(=[S:56])[NH2:38]

Participants

Conditions

Temperature: 50 °C

Procedure

Succinic acid 4-carbamoyl-phenyl ester 2-{2-[8-(2,2-dimethyl-butyryloxy)-2,6-dimethyl-1,2,6,7,8,8a-hexahydro-naphthalen-1-yl]-ethyl}-6-oxo-tetrahydro-pyran-4-yl ester (2) (0.35 g, 0.000548 mol) and Lawesson reagent (0.221 g, 0.000548 mol) were dissolved in 30 ml of anhydrous benzene. The reaction was warmed to 50° C. and stirred for 6 h. The solvent was removed under reduced pressure; the crude residue was purificated by silica gel column (dichloromethane/methyl alcohol 9.5:0.5) to furnish 35 mg of the pure compound 3 (10% yield).

Workup

customThe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-a1032e63b4334dd8bfa433f429719998
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08314140B2

Reaction notes

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