Dimethyl Sulfoxide → Biphenyl-2-ylcarbamic Acid 1-(2-{[4-(4-Formyl-2,5-dimethylphenylcarbamoyl)butyl]methylcarbamoyl}ethyl)piperidin-4-yl Ester

HRID 2412278Notes

Reaction equation

[OH:1][CH2:2][C:3]1[C:8]([CH3:9])=[CH:7][C:6]([NH:10][C:11]([CH2:13][CH2:14][CH2:15][CH2:16][N:17]([CH3:44])[C:18]([CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][CH:25]([O:28][C:29](=[O:43])[NH:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[CH2:24][CH2:23]2)=[O:19])=[O:12])=[C:5]([CH3:45])[CH:4]=1.CS(C)=O.C(N(CC)C(C)C)(C)C.O>C(Cl)Cl>[CH:2]([C:3]1[C:8]([CH3:9])=[CH:7][C:6]([NH:10][C:11]([CH2:13][CH2:14][CH2:15][CH2:16][N:17]([CH3:44])[C:18]([CH2:20][CH2:21][N:22]2[CH2:23][CH2:24][CH:25]([O:28][C:29](=[O:43])[NH:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[CH2:26][CH2:27]2)=[O:19])=[O:12])=[C:5]([CH3:45])[CH:4]=1)=[O:1]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of biphenyl-2-ylcarbamic acid 1-(2-{[4-(4-hydroxymethyl-2,5-dimethylphenylcarbamoyl)butyl]methylcarbamoyl}ethyl)piperidin-4-yl ester (0.460 g, 0.748 mmol) and dimethyl sulfoxide (0.531 mL, 7.48 mmol) in DCM (2.58 mL) at 0° C. was added N,N-diisopropylethylamine (0.65 mL, 3.7 mmol). Sulfur trioxide pyridine complex (0.357 g, 2.24 mmol) was added and the resulting mixture was stirred at 0° C. for 1 h. Water (3 mL) was added and the layers were separated. The organic layer was dried over sodium sulfate and filtered to give the title compound in a DCM solution, which was used immediately in the next reaction.

Workup

additionSulfur trioxide pyridine complex (0.357 g, 2.24 mmol) was added
customthe layers were separated
dry with materialThe organic layer was dried over sodium sulfate
filtrationfiltered

Sources & evidence

ORD record: ord-1e47a67dc898453a9ecc376066e4ec6a
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08816088B2

Reaction notes

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