Hydroxyamine hydrochloride → HCID 20712351, compound

HRID 2269315Notes

Reaction equation

HRID 2269315 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([N:18]2[CH2:23][C:22]3([CH3:26])[CH2:24][CH2:25][CH:19]2[C:20](=[O:27])[O:21]3)(=[O:17])=[O:16])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O-].[Na+].Cl.[NH2:32][OH:33]>NO.CO.Cl>[OH:33][NH:32][C:20]([CH:19]1[CH2:25][CH2:24][C:22]([OH:21])([CH3:26])[CH2:23][N:18]1[S:15]([C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:10][CH:11]=1)(=[O:17])=[O:16])=[O:27]

Participants

7

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 10942334Sodium MethoxideHCID 17967911HCID 17967911, compound

Product 1

HCID 20712351HCID 20712351, compoundYield 71.3%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 787HydroxylamineSolventHCID 887MethanolSolvent2×

Conditions

Temperature
60 °C

Procedure

5-(4-Benzyloxy-benzenesulfonyl)-1-methyl-2-oxa-5-aza-bicyclo[2.2.2]octan-3-one (0.035 g, 0.09 mmol) was dissolved in 0.80 mL of a 0.81 M solution of hydroxylamine in methanol (prepared by treating 7.25 mL of a 0.81 M solution of sodium methoxide in methanol with 0.52 g of hydroxylamine hydrochloride). The resulting mixture was shaken at 60° C. for 10 minutes. After cooling to room temperature, the mixture was diluted with 1M HCl, extracted twice with ethyl acetate, and the combined organic layers were washed twice with 50% saturated aqueous NaHCO3, once with 1M pH 7.0 phosphate buffer, dried over Na2SO4, filtered and concentrated in vacuo. Trituration of the residue with CH2Cl2-hexane afforded 0.027 g of 1-(4-benzyloxy-benzenesulfonyl)-5-hydroxy-5-methyl-piperidine-2-carboxylic acid hydroxyamide as a colorless solid:

Workup

  1. customprepared
  2. temperatureAfter cooling to room temperature
  3. extractionextracted twice with ethyl acetate
  4. washthe combined organic layers were washed twice with 50% saturated aqueous NaHCO3, once with 1M pH 7.0 phosphate buffer
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-545befd3ce3544e0a40ae7dc74a5ff13
Source dataset
uspto-grants-2001_12
Patent number
US06329397B1

Reaction notes

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