Hydrochloric Acid → HCID 22915504, compound

HRID 1377920Notes

Reaction equation

HRID 1377920 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][CH2:10]C(O)=O)=[CH:4][CH:3]=1.CN1CC[O:18][CH2:17]C1.ClC(OCC(C)C)=O.[C:29]([O:33][NH2:34])([CH3:32])([CH3:31])[CH3:30].Cl.[OH-].[Na+].[NH4+].[Cl-]>C1COCC1.O.C(OCC)C>[C:29]([O:33][NH:34][C:17](=[O:18])[CH:9]([S:8][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=1)[CH3:10])([CH3:32])([CH3:31])[CH3:30]

Participants

11

Reactant 7

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 62365Isobutyl chloroformateHCID 2777907O-tert-butylhydroxylamineHCID 167762423-(4-Bromothiophenoxy)propionic acid

Product 1

HCID 22915504HCID 22915504, compoundYield 60%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution in THF (100 mL) of 3-(4-bromophenylthio)propanoic acid (6.88 g, 26.5 mmol) was added 4-methylmorpholine (2.94 g, 29.2 mmol) and isobutyl chloroformate (3.6 g, 29.2 mmol) and the reaction mixture was stirred for 1 hour. To the reaction mixture was added aqueous O-tert-butylhydroxylamine (39.8 mmol; prepared by dissolving the hydrochloride in water and adding 3M NaOH to give the free base) and the reaction mixture was stirred overnignt at ambient temperature. The reaction mixture was poured into a mixture of ethyl ether and saturated aqueous NH4Cl. The aqueous phase was extracted with ethyl ether. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. Chromatography on silica gel (30% ethyl acetate-hexanes) gave O-tert-butyl-2-(4-bromophenylthio)propanohydroxamic acid (5.36 g, 60%).

Workup

  1. customprepared
  2. customto give the free base) and the reaction mixture
  3. stirringwas stirred overnignt at ambient temperature
  4. extractionThe aqueous phase was extracted with ethyl ether
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-50e7c793954b4db59dbee4ed2ddea4c7
Source dataset
uspto-grants-1997_09
Patent number
US05665777

Reaction notes

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