Imidazole → HCID 131735330, compound

HRID 627663Notes

Reaction equation

N1C=CN=C1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[I:25]I.[C:27]([O:31][C:32](=[O:65])[N:33]([C:41]1[C:42]([CH3:64])([CH3:63])[S:43](=[O:62])(=[O:61])[CH2:44][C@:45]([C:48]2[CH:53]=[C:52]([N+:54]([O-:56])=[O:55])[CH:51]=[CH:50][C:49]=2[CH2:57][CH2:58][CH2:59]O)([CH3:47])[N:46]=1)[C:34]([O:36]C(C)(C)C)=[O:35])([CH3:30])([CH3:29])[CH3:28]>C(Cl)Cl>[C:27]([O:31][C:32](=[O:65])[NH:33][C:41]1[C:42]([CH3:64])([CH3:63])[S:43](=[O:62])(=[O:61])[CH2:44][C@:45]([C:48]2[CH:53]=[C:52]([N+:54]([O-:56])=[O:55])[CH:51]=[CH:50][C:49]=2[CH2:57][CH2:58][CH2:59][I:25])([CH3:47])[N:46]=1)([CH3:30])([CH3:29])[CH3:28].[C:27]([O:31][C:32]([NH:33][C:34](=[O:35])[O-:36])=[O:65])([CH3:30])([CH3:28])[CH3:29]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of imidazole (64.5 mg, 0.948 mmol) and triphenylphosphine (99 mg, 0.379 mmol) in 1.5 ml DCM was cooled to 0° C. and iodine (96 mg, 0.379 mmol) was added. The mixture was stirred for 2 min at 0° C., then solution of (R)-tert-butyl-N-(5-(2-(3-hydroxypropyl)-5-nitrophenyl)-2,2,5-trimethyl-1,1-dioxido-5,6-dihydro-2H-1,4-thiazin-3-yl)-N-tert-butoxycarbonyl-carbamate (180 mg, 0.316 mmol) in 0.5 ml DCM was added. The mixture was removed from cooling bath and stirred at rt for 20 min. The mixture was directly loaded onto 12 g RediSep Gold column and eluted with 5-50% EtOAc in heptane to afford (R)-tert-butyl-N-(5-(2-(3-iodopropyl)-5-nitrophenyl)-2,2,5-trimethyl-1,1-dioxido-5,6-dihydro-2H-1,4-thiazin-3-yl)carbamate-N-tert-butoxycarbonyl-carbamate (173 mg, 0.255 mmol, 81% yield). LC/MS (ESI+) m/z=524 (M Boc−t-Bu).

Workup

customThe mixture was removed
temperaturefrom cooling bath
stirringstirred at rt for 20 min
washeluted with 5-50% EtOAc in heptane

Sources & evidence

ORD record: ord-250c528d7bf041f389a0b3d53a326817
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309263B2

Reaction notes

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