Dimethylformamide → N-hydroxy-3-(4-methoxyphenylsulfanyl)-4-phenylbutyramide

HRID 1107114Notes

Reaction equation

HRID 1107114 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][CH:10]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:11][C:12](O)=[O:13])=[CH:5][CH:4]=1.CN(C=O)C.C(Cl)(=O)C(Cl)=O.C[Si](C)(C)[O:35][NH2:36]>C(Cl)Cl>[OH:35][NH:36][C:12](=[O:13])[CH2:11][CH:10]([S:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 2734666O-(Trimethylsilyl)hydroxylamineHCID 106381083-(4-Methoxyphenylsulfanyl)-4-phenylbutyric acid

Product 1

HCID 10567497N-hydroxy-3-(4-methoxyphenylsulfanyl)-4-phenylbutyramideYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

To a solution of 1 g (3.31 mmol) of 3-(4-methoxyphenylsulfanyl)-4-phenylbutyric acid in 30 mL of CH2Cl2 at 25° C. under argon is added 0.2 mL of DMF followed by 4.1 mL (8.27 mmol) of 2 M solution of oxalyl chloride in CH2Cl2. After stirring at 25° C. for 1.5 hours, 2.1 mL (16.53 mmol) of O-trimethylsilylhydroxylamine is added and this 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. Purification by flash silica gel chromatography affords 0.86 g (82%) of N-hydroxy-3-(4-methoxyphenylsulfanyl)-4-phenylbutyramide as a yellow crystalline solid.

Workup

  1. stirringthis is then stirred at 25° C. for 18 hours
  2. customThe reaction is partitioned between CH2Cl2 and 1 N HCl
  3. dry with materialThe organic layer is dried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo
  5. customPurification by flash silica gel chromatography

Sources & evidence

ORD record
ord-b9cb22066b264e21a47a1f34cc01aa57
Source dataset
uspto-grants-2000_05
Patent number
US06057369

Reaction notes

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