Dimethylformamide → N-hydroxy-3-(3,4-dimethoxyphenylsulfanyl)-4-phenylbutyramide

HRID 1107142Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:11][CH:12]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:13][C:14](O)=[O:15])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].CN(C=O)C.C(Cl)(=O)C(Cl)=O.C[Si](C)(C)[O:37][NH2:38]>C(Cl)Cl>[OH:37][NH:38][C:14](=[O:15])[CH2:13][CH:12]([S:11][C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 2 g (6.02 mmol) of 3-(3,4-dimethoxyphenylsulfanyl)-4-phenylbutanoic acid in 50 mL of CH2Cl2 at 25° C. under argon is added 0.2 mL of DMF followed by 6.02 mL (12.03 mmol, 2 eq) of 2 M solution of oxalyl chloride in CH2Cl2. After stirring at 25° C. for 3 hours, the mixture is cooled to 0° C. and 3.7 mL (30.08 mmol, 5 eq) of O-trimethylsilylhydroxylamine is added. This mixture is then stirred at 25° C. for 18 hours. The reaction is partitioned between CH2Cl2 and 1 N HCl. The organic layer is dried over anhydrous Na2SO4 and concentrated in vacuo. The product is purificatied by flash silica gel chromatography to afford N-hydroxy-3-(3,4-dimethoxyphenylsulfanyl)-4-phenylbutyramide as a yellow crystalline solid. (1.7 g, 81%): 1H-NMR (300 MHz, DMSO-d6) δ (TMS) 2.2(m, 2H), 2.81 (m, 2H), 3.6(m, 1H), 3.75(s, 6H), 6.89-7 (m, 3H), 7.17-7.35(m, 5H), 8.85(s, 1H), 10.5(s, 1H).

Workup

temperaturethe mixture is cooled to 0° C.
stirringThis mixture is then stirred at 25° C. for 18 hours
customThe reaction is partitioned between CH2Cl2 and 1 N HCl
dry with materialThe organic layer is dried over anhydrous Na2SO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-fafe4b5159694dc4bfafd9289c0a2f90
Source dataset: uspto-grants-2000_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06057369

Reaction notes

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