2,4,6-Tris(1-methylethyl)benzenesulfonyl chloride → [1-({4-[(2-Fluoro-4-iodophenyl)amino]-3-thienyl}carbonyl)-3-hydroxyazetidin-3-yl]methyl 2,4,6-tris(1-methylethyl)benzenesulfonate

HRID 1809014Notes

Reaction equation

HRID 1809014 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[C:11]([C:15]([N:17]2[CH2:20][C:19]([CH2:22][OH:23])([OH:21])[CH2:18]2)=[O:16])=[CH:12][S:13][CH:14]=1.[CH:24]([C:27]1[CH:32]=[C:31]([CH:33]([CH3:35])[CH3:34])[CH:30]=[C:29]([CH:36]([CH3:38])[CH3:37])[C:28]=1[S:39](Cl)(=[O:41])=[O:40])([CH3:26])[CH3:25]>ClCCl.CN(C)C1C=CN=CC=1>[CH3:26][CH:24]([C:27]1[CH:32]=[C:31]([CH:33]([CH3:34])[CH3:35])[CH:30]=[C:29]([CH:36]([CH3:38])[CH3:37])[C:28]=1[S:39]([O:23][CH2:22][C:19]1([OH:21])[CH2:18][N:17]([C:15]([C:11]2[C:10]([NH:9][C:3]3[CH:4]=[CH:5][C:6]([I:8])=[CH:7][C:2]=3[F:1])=[CH:14][S:13][CH:12]=2)=[O:16])[CH2:20]1)(=[O:40])=[O:41])[CH3:25]

Participants

5

Reactant 2

HCID 810422,4,6-Tris(1-methylethyl)benzenesulfonyl chlorideHCID 670515741-({4-[(2-Fluoro-4-iodophenyl)amino]-3-thienyl}carbonyl)-3-(hydroxymethyl)azetidin-3-ol

Product 1

HCID 86621271[1-({4-[(2-Fluoro-4-iodophenyl)amino]-3-thienyl}carbonyl)-3-hydroxyazetidin-3-yl]methyl 2,4,6-tris(1-methylethyl)benzenesulfonateYield 26%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

1-({4-[(2-Fluoro-4-iodophenyl)amino]-3-thienyl}carbonyl)-3-(hydroxymethyl)azetidin-3-ol (247 mg, 0.551 mmol), was suspended in dichloromethane (10 mL) and treated with 4-(dimethylamino)pyridine (80 mg, 0.661 mmol), and 2,4,6-triisopropylbenzenesulfonyl chloride (183 mg, 0.604 mmol) at ambient for 15 h. The mixture was adsorbed on to silica and purified by column chromatography (silica gel, 30% ethyl acetate in hexanes) to give [1-({4-[(2-fluoro-4-iodophenyl)amino]-3-thienyl}carbonyl)-3-hydroxyazetidin-3-yl]methyl 2,4,6-tris(1-methylethyl)benzenesulfonate (101 mg, 0.141 mmol, 26% yield): MS (EI) for C30H36FIN2O5S2: 715 (MH+).

Workup

  1. custompurified by column chromatography (silica gel, 30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-f1f3e92f279d484494093ab576ccf8a0
Source dataset
uspto-grants-2013_01
Patent number
US08362002B2

Reaction notes

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