2,2-Dimethoxypropane → 3-[4-(4-Bromophenyl)-1,3-thiazol-2-yl]-2,2-dimethyl-1,3-oxazolidin-4-one

HRID 1436411Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([NH:13][C:14](=[O:17])[CH2:15][OH:16])[S:11][CH:12]=2)=[CH:4][CH:3]=1.CO[C:20](OC)([CH3:22])[CH3:21].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]([N:13]3[C:14](=[O:17])[CH2:15][O:16][C:20]3([CH3:22])[CH3:21])[S:11][CH:12]=2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 90 °C

Procedure

N-[4-(4-Bromophenyl)-1,3-thiazol-2-yl]-2-hydroxyacetamide (0.35 g, 1.12 mmol), prepared in the previous step, was suspended in 10 mL of toluene, dimethoxypropane (2.0 mL, 16.7 mmol) was added, which was followed by a catalytic amount of p-toluenesulfonic acid monohydrate (20 mg). The mixture was heated to 90° C. for 16 h, then cooled and concentrated under reduced pressure. Flash chromatography (5% acetone/hexane) provided the title compound (210 mg, 53%) as a white solid. HRMS: calcd for C14H13BrN2O2S+H+, 352.99538; found (ESI, [M+H]+), 352.9957. Analytical HPLC: retention time 11.1 min, 210-370 nm the Xterra® RP18 column, 3.5μ, 150×4.6 mm 40° C. 85/15-5/95 (Ammon. Form. Buff. pH=3.5/ACN+MeOH) for 10 min, hold 4 min, 1.2 mL/min 5 μL injection.

Workup

temperaturecooled
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-2cfca32a25de4436abd344d4efd6518d
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07618990B2

Reaction notes

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