Methyl N-(triethylammoniosulfonyl)carbamate → Methyl 6-[(4-bromo-2-fluorophenyl)methyl]-5-methyl-1,1-dioxo-1lambda6,2,6-thiadi-azinane-2-carboxylate

HRID 1403731Notes

Reaction equation

[Br:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][NH:7][CH:8]([CH3:12])[CH2:9][CH2:10]O)=[C:4]([F:15])[CH:3]=1.CC[N+]([S:23]([N:26]=[C:27]([O:29][CH3:30])[O-:28])(=[O:25])=[O:24])(CC)CC>C1COCC1>[Br:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][N:7]2[S:23](=[O:25])(=[O:24])[N:26]([C:27]([O:29][CH3:30])=[O:28])[CH2:10][CH2:9][CH:8]2[CH3:12])=[C:4]([F:15])[CH:3]=1

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of 3-(4-bromo-2-fluorobenzylamino)butan-1-ol (800 mg, 2.9 mmol) and Burgess' Reagent (2.07 g, 8.7 mmol) in anhydrous THF (10 mL) was heated at 65° C. for 2 hours. The reaction mixture was concentrated under reduced pressure. The crude product was purified by silica gel chromatography using petroleumn ether/EtOAc (6/1) as eluting solvents to afford methyl 6-[(4-bromo-2-fluorophenyl)methyl]-5-methyl-1,1-dioxo-1λ6,2,6-thiadi-azinane-2-carboxylate as light yellow oil. (900 mg, 79%). 1H NMR (500 MHz, CDCl3) δ 7.45 (t, 1H), 7.17 (d, 1H), 7.25-7.23 (m, 1H), 4.44 (dd, 2H), 4.20-4.25 (m, 1H), 3.92-3.99 (m, 1H), 3.88 (s, 3H), 3.45-3.51 (m, 1H), 1.87-2.00 (m, 2H), 1.23 (d, 3H); LCMS (ESI): m/z=397.0 [M+H]+.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customThe crude product was purified by silica gel chromatography
washas eluting solvents

Sources & evidence

ORD record: ord-25b947c5eac149789595190e33fbb34a
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912219B2

Reaction notes

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