Iodine → HCID 59339877, compound

HRID 1098996Notes

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-8a72deabc13541379bbfbda92fd4f4d6
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08143290B2

Reaction notes

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