Chloroacetone → HCID 21093960, compound

HRID 729734Notes

Reaction equation

[SH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:17][CH:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[C:9]([NH:11][C:12]2[S:13][CH:14]=[CH:15][N:16]=2)=[O:10])=[CH:4][CH:3]=1.Cl[CH2:25][C:26](=[O:28])[CH3:27]>>[O:28]=[C:26]([CH3:27])[CH2:25][S:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:17][CH:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[C:9]([NH:11][C:12]2[S:13][CH:14]=[CH:15][N:16]=2)=[O:10])=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 6571Chloroacetone

HCID 21093996HCID 21093996, compound

Product 1

HCID 21093960HCID 21093960, compound

Procedure

Reaction of 2-(4-mercaptophenyl)-3-(tetrahydropyran-4-yl)-N-thiazol-2-ylpropionamide (see EXAMPLE 146, 363 mg, 1.04 mmol) with chloroacetone (90 μL, 1.10 mmol) employing a procedure similar to that described in EXAMPLE 146, furnished 2-[4-(2-oxopropylsulfanyl)phenyl]-3-(tetrahydropyran-4-yl)-N-thiazol-2-ylpropionamide: m/z (ES+)=405.3 [M+H]+. TBA-OX (2.46 g, 2.44 mmol) was added to a stirred solution of the abovementioned thioether (399 mg, 0.99 mmol) in CH2Cl2 (20 mL). After 19 h, the reaction mixture was treated with more TBA-OX (0.97 g, 0.96 mmol). An additional quantity of TBA-OX (1.09 g, 1.07 mmol) was added 20 h later, then the mixture was stirred further for 3 d. Solvent evaporation and flash chromatography (IH-EtOAc, 3:2 to 0:1) afforded the title compound: RTA=3.12 min; m/z (ES+)=437.2 [M+H]+.

Sources & evidence

ORD record: ord-1dbab1d675f74ae798df99f1ecf584dd
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07582632B2

Reaction notes

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