Lawesson's reagent → HCID 86648333, compound

HRID 1253888Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:14][C:13]2[CH:15]=[CH:16][C:17]([F:19])=[CH:18][C:12]=2[NH:11][C:10](=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:30])=CC=1>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:14][C:13]2[CH:15]=[CH:16][C:17]([F:19])=[CH:18][C:12]=2[NH:11][C:10](=[S:30])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 8-fluoro-2-oxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepine-4-carboxylic acid tert-butyl ester (3.24 g, 11.57 mmol) in toluene (50 mL), was added Lawesson's reagent (2.33 g, 5.78 mmol) at r.t. The reaction mixture was heated at 90° C. for 30-40 min. After completion of reaction, as confirmed by TLC, distilled water (50 mL) was added and the crude compound was extracted with EtOAc (3×50 mL). The combined organic layers were dried over Na2SO4. The solvents were removed in vacuo to afford the crude compound, which was purified by column chromatography (silica gel, 2:8 EtOAc:Pet. ether) to afford pure 8-fluoro-2-thioxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepine-4-carboxylic acid tert butyl ester (2.36 g, 69%) as light Yellow solid.

Workup

customAfter completion of reaction
distillationdistilled water (50 mL)
additionwas added
extractionthe crude compound was extracted with EtOAc (3×50 mL)
dry with materialThe combined organic layers were dried over Na2SO4
customThe solvents were removed in vacuo
customto afford the crude compound, which
customwas purified by column chromatography (silica gel, 2:8 EtOAc:Pet. ether)

Sources & evidence

ORD record: ord-1a00449a7a18436390200ac2f08ae33f
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08455479B2

Reaction notes

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