Hexane → HCID 25029879, compound

HRID 1436419Notes

Reaction equation

C(N(CC)C(C)C)(C)C.[N+:10]([C:13]1[CH:18]=[CH:17][C:16]([C:19]2[N:20]=[C:21]([NH:24][C:25]([CH3:29])([CH3:28])[CH2:26][OH:27])[S:22][CH:23]=2)=[CH:15][CH:14]=1)([O-:12])=[O:11].Cl[C:31](Cl)([O:33]C(=O)OC(Cl)(Cl)Cl)Cl.CCCCCC>C(Cl)Cl.C(OCC)(=O)C>[CH3:28][C:25]1([CH3:29])[CH2:26][O:27][C:31](=[O:33])[N:24]1[C:21]1[S:22][CH:23]=[C:19]([C:16]2[CH:15]=[CH:14][C:13]([N+:10]([O-:12])=[O:11])=[CH:18][CH:17]=2)[N:20]=1

Participants

Conditions

Temperature: 0 °C

Procedure

N,N-diisopropylethylamine (1.0 mL, 5.7 mmol) was added dropwise to a solution of 2-{[4-(4-nitrophenyl)-1,3-thiazol-2-yl]amino}-2-methylpropan-1-ol (0.7 g, 2.4 mmol), prepared in the previous step, in 20 mL of dry methylene chloride at 0° C., followed by triphosgene (0.8 g, 2.8 mmol) in 20 mL of dry dichloromethane. The orange solution was stirred at 0° C. for 3 h, and then allowed to warm to room temperature. TLC (3:1 hexane:ethyl acetate) indicated the reaction was complete. The reaction was washed with 2N HCl and the aqueous layer was extracted with methylene chloride. The combined organic layer was dried (anhydrous MgSO4), filtered and concentrated under reduced pressure to give 900 mg of a yellow solid. Purification of the solid on silica gel using a stepwise gradient of 6:1 to 5:1 hexane:ethyl acetate gave the title compound (268 mg, 35%), mp 176-179° C.

Workup

temperatureto warm to room temperature
washThe reaction was washed with 2N HCl
extractionthe aqueous layer was extracted with methylene chloride
dry with materialThe combined organic layer was dried (anhydrous MgSO4)
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-6e5c50a76b1646cabc3818bb49bc3c48
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07618990B2

Reaction notes

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