Triethylamine → Ethyl 2,4,6-tri(propan-2-yl)benzenesulfonate

HRID 605764Notes

Reaction equation

FC1C(NC2C=CC(I)=CC=2F)=C(C(N2CC(C(O)CC3OCCO3)(O)C2)=O)C=CC=1F.C(N(CC)CC)C.[CH:40]([C:43]1[CH:48]=[C:47]([CH:49]([CH3:51])[CH3:50])[CH:46]=[C:45]([CH:52]([CH3:54])[CH3:53])[C:44]=1[S:55](Cl)(=[O:57])=[O:56])([CH3:42])[CH3:41].C([O:62][CH2:63][CH3:64])(=O)C>ClCCl.CN(C)C1C=CN=CC=1>[CH3:42][CH:40]([C:43]1[CH:48]=[C:47]([CH:49]([CH3:50])[CH3:51])[CH:46]=[C:45]([CH:52]([CH3:54])[CH3:53])[C:44]=1[S:55]([O:62][CH2:63][CH3:64])(=[O:56])=[O:57])[CH3:41]

Participants

Conditions

Temperature: 35 °C

Procedure

1-({3,4-Difluoro-2-[(2-fluoro-4-iodophenyl)amino]phenyl}carbonyl)-3-[2-(1,3-dioxolan-2-yl)-1-hydroxyethyl]azetidin-3-ol (148 mg, 0.262 mmol), was dissolved in dichloromethane (10 mL) and treated with 4-(dimethylamino)pyridine (38 mg, 0.31 mmol), triethylamine (0.036 mL, 0.262 mmol) and 2,4,6-triisopropylbenzenesulfonyl chloride (303 mg, 1.0 mmol) at 35° C. for 15 h. 2,4,6-Triisopropylbenzenesulfonyl chloride (100 mg, 0.33 mmol) was added and the mixture was stirred at 35° C. for 3.5 h. The mixture was adsorbed on to silica and purified by column chromatography (silica gel, 40-50% ethyl acetate in hexanes and then 100% ethyl acetate) to give 1-[1-({3,4-difluoro-2-[(2-fluoro-4-iodophenyl)amino]phenyl}carbonyl)-3-hydroxyazetidin-3-yl]-dioxolan-2-yl)ethyl 2,4,6-tris(1-methylethyl)benzenesulfonate (30 mg, 0.0361 mmol, 14% yield): MS (EI) for C36H42F3IN2O7S: 831 (MH+).

Workup

custompurified by column chromatography (silica gel, 40-50% ethyl acetate in hexanes

Sources & evidence

ORD record: ord-b7df96bd961342f8bb81b276b586ac30
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07915250B2

Reaction notes

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