Iodine → HCID 59339877, compound

HRID 13227Notes

Reaction equation

[Mg].Br[C:3]1[CH:8]=[CH:7][C:6]([S:9][CH3:10])=[C:5]([O:11][CH3:12])[CH:4]=1.II.CON(C)[C:18](=[O:29])[C@@H:19]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH3:20]>O1CCCC1>[CH3:12][O:11][C:5]1[CH:4]=[C:3]([C:18](=[O:29])[C@H:19]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:26])([CH3:25])[CH3:27])[CH3:20])[CH:8]=[CH:7][C:6]=1[S:9][CH3:10]

Participants

Conditions

Temperature: 60 °C

Procedure

Magnesium (17 μg, 0.69 mmol) was placed in a screwcap reaction tube, and a solution of (4-bromo-2-methoxyphenyl)(methyl)sulfane (308e, 100 μg, 0.43 mmol) in tetrahydrofuran (1 mL) was added, followed by a small crystal of iodine. The tube was sealed and flushed with argon. The mixture was stirred at 60° C. overnight. After cooling (S)-tert-butyl 1-(methoxy(methyl)amino)-1-oxopropan-2-ylcarbamate (35 μg, 150 μmol) was added as a solid, and the mixture was stirred at r.t. for 1 h. Then the solvent was evaporated, the mixture was partitioned between aq. HCl (1N) and ethyl acetate. The organic layer was separated and dried. The product was isolated by HPLC to afford 10 mg (10%).

Workup

customThe tube was sealed
customflushed with argon
additionwas added as a solid
stirringthe mixture was stirred at r.t. for 1 h
customThen the solvent was evaporated
customthe mixture was partitioned between aq. HCl (1N) and ethyl acetate
customThe organic layer was separated
customdried
customThe product was isolated by HPLC
customto afford 10 mg (10%)

Sources & evidence

ORD record: ord-b5d2740942c84dfd9c3a31d1fab0cb15
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07728030B2

Reaction notes

Loading…