Dimethylformamide → N-hydroxy-2(R)-[(3,4-methylenedioxybenzyl)-(4-methoxy-2,3,6-trimethylbenzenesulfonyl)amino]-3-methylbutyramide

HRID 2297971Notes

Reaction equation

HRID 2297971 reaction equation
[CH2:1]1[O:32][C:31]2[CH:30]=[CH:29][C:5]([CH2:6][N:7]([S:15]([C:18]3[C:23]([CH3:24])=[CH:22][C:21]([O:25][CH3:26])=[C:20]([CH3:27])[C:19]=3[CH3:28])(=[O:17])=[O:16])[C@H:8]([CH:12]([CH3:14])[CH3:13])[C:9](O)=[O:10])=[CH:4][C:3]=2[O:2]1.C(Cl)(=O)C(Cl)=O.CN(C)C=O.C[Si](C)(C)[NH:46][O:47][Si](C)(C)C>C(Cl)Cl.CO>[OH:47][NH:46][C:9](=[O:10])[C@H:8]([N:7]([CH2:6][C:5]1[CH:29]=[CH:30][C:31]2[O:32][CH2:1][O:2][C:3]=2[CH:4]=1)[S:15]([C:18]1[C:23]([CH3:24])=[CH:22][C:21]([O:25][CH3:26])=[C:20]([CH3:27])[C:19]=1[CH3:28])(=[O:17])=[O:16])[CH:12]([CH3:14])[CH3:13]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 898151,1,1-trimethyl-N-((trimethylsilyl)oxy)silylamineHCID 114311912(R)-[(3,4-methylenedioxybenzyl)-(4-methoxy-2,3,6-trimethyl-benzenesulfonyl)amino]-3-methylbutyric acid

Product 1

HCID 9934789N-hydroxy-2(R)-[(3,4-methylenedioxybenzyl)-(4-methoxy-2,3,6-trimethylbenzenesulfonyl)amino]-3-methylbutyramideYield 62.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2(R)-[(3,4-methylenedioxybenzyl)-(4-methoxy-2,3,6-trimethylbenzenesulfonyl)amino]-3-methylbutyric acid (3.82 g, 8.24 mmol) in dry methylene chloride (20 mL) was added oxalyl chloride (2.2 mL, 24.72 mmol) and a drop of dimethylformamide. The reaction mixture was stirred for 4 h and then concentrated. The residue was dissolved in methylene chloride 20 mL) and N,O-bis-trimethylsilylhydroxylamine (8.8 mL, 41.2 mmol) was added. After 4 h, methanol (1 mL) was added and the stirring was continued for 30 min. Silica gel (10 g) was added and the material was concentrated to dryness. The resultant powder was flash chromatographed on a silica gel column and eluted with 50% ethyl acetate/hexanes to give N-hydroxy-2(R)-[(3,4-methylenedioxybenzyl)-(4-methoxy-2,3,6-trimethylbenzenesulfonyl)amino]-3-methylbutyramide (2.46 g).

Workup

  1. concentrationconcentrated
  2. additionwas added
  3. waitAfter 4 h
  4. waitthe stirring was continued for 30 min
  5. additionSilica gel (10 g) was added
  6. concentrationthe material was concentrated to dryness
  7. customchromatographed on a silica gel column
  8. washeluted with 50% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-83d22a4fb6a547b18f025d50921bf66c
Source dataset
uspto-grants-2002_12
Patent number
US06492394B1

Reaction notes

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