Lawesson's reagent → HCID 76831279, compound

HRID 1186171Notes

Reaction equation

[C:1](=[N:14][C:15]1[CH:16]=[CH:17][C:18]([F:30])=[C:19]([C:21]23[CH2:28][CH:27]2[CH2:26][O:25][CH2:24][C:23](=O)[NH:22]3)[CH:20]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:40]2)=CC=1.C([O-])(O)=O.[Na+]>O1CCOCC1>[C:1](=[N:14][C:15]1[CH:16]=[CH:17][C:18]([F:30])=[C:19]([C:21]23[CH2:28][CH:27]2[CH2:26][O:25][CH2:24][C:23](=[S:40])[NH:22]3)[CH:20]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of (1SR,7RS)-1-[5-(benzhydrylidene-amino)-2-fluoro-phenyl]-5-oxa-2-aza-bicyclo[5.1.0]octan-3-one (intermediate B11A) (460 mg, 1.15 mmol) in dioxane (3 ml) at 23° C. was added 2,4-bis-(4-methoxy-phenyl)-[1,3,2,4]dithiadiphosphetane 2,4-disulfide (Lawesson's reagent) (292 mg, 0.72 mmol) and the mixture was stirred at 80° C. for 2 h. The green solution was poured on sat. NaHCO3 solution, extracted with ethyl acetate, washed the organic layer with brine and dried over sodium sulfate. Removal of the solvent in vacuum left the title compound as a green oil (600 mg, ca. 80% pure, 100%), which was used in the next step without further purification. MS (ISP): m/z=417.3 [(M+H)+].

Workup

extractionextracted with ethyl acetate
washwashed the organic layer with brine
dry with materialdried over sodium sulfate
customRemoval of the solvent in vacuum
waitleft the title compound as a green oil (600 mg, ca. 80% pure, 100%), which
customwas used in the next step without further purification

Sources & evidence

ORD record: ord-8fae6fdb41674d34aae730c4c0eff121
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673894B2

Reaction notes

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