Hydroxyamine hydrochloride → HCID 73508098, compound

HRID 2259651Notes

Reaction equation

HRID 2259651 reaction equation
OC1[O:6][CH:5]([C:7]2[S:8][C:9]3[CH:15]=[C:14]([N:16]4[CH2:20][CH:19]([CH2:21][O:22][CH3:23])[O:18][C:17]4=[O:24])[CH:13]=[CH:12][C:10]=3[N:11]=2)[CH2:4][CH2:3]1.Cl.[NH2:26][OH:27]>N1C=CC=CC=1>[OH:6][CH:5]([C:7]1[S:8][C:9]2[CH:15]=[C:14]([N:16]3[CH2:20][CH:19]([CH2:21][O:22][CH3:23])[O:18][C:17]3=[O:24])[CH:13]=[CH:12][C:10]=2[N:11]=1)[CH2:4][CH:3]=[N:26][OH:27]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 15342529HCID 15342529, compound

Product 1

HCID 73508098HCID 73508098, compoundYield 101.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

72 g of the 3-[2-(5-hydroxytetrahydrofuran-2-yl)-benzothiazol-6-yl]-5-methoxymethyl-2-oxazolidinone obtained in the Example 7 was dissolved in 150 ml of pyridine. 18.6 g of hydroxylamine hydrochloride was added to the solution at room temperature and the mixture was stirred for 10 min and then poured into ice/water. After extraction with ethyl acetate followed by washing with dilute hydrochloric acid, an aqueous sodium hydrogencarbonate solution and an aqueous common salt solution, the product was dried over magnesium sulfate. After concentration under reduced pressure, the obtained solid was recrystallized from acetone/diisopropyl ether to give 73 g of the titled compound.

Workup

  1. extractionAfter extraction with ethyl acetate
  2. washby washing with dilute hydrochloric acid
  3. dry with materialan aqueous sodium hydrogencarbonate solution and an aqueous common salt solution, the product was dried over magnesium sulfate
  4. concentrationAfter concentration under reduced pressure
  5. customthe obtained solid was recrystallized from acetone/diisopropyl ether

Sources & evidence

ORD record
ord-98c84408806d4feeb0670a114455b46e
Source dataset
uspto-grants-1995_12
Patent number
US05475014

Reaction notes

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