Hydroxyamine hydrochloride → HCID 88162749, compound

HRID 975940Notes

Reaction equation

HRID 975940 reaction equation
Cl.[NH2:2][OH:3].[C:4]([C:7]1[CH:8]=[C:9]([NH:13][C:14](=[O:37])[NH:15][CH2:16][C:17]([N:19]2[CH:30]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH2:29][CH2:28][CH:20]2[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[O:18])[CH:10]=[CH:11][CH:12]=1)(=O)[CH3:5]>O.CO.N1C=CC=CC=1>[OH:3]/[N:2]=[C:4](/[C:7]1[CH:8]=[C:9]([NH:13][C:14](=[O:37])[NH:15][CH2:16][C:17]([N:19]2[CH:30]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH2:29][CH2:28][CH:20]2[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[O:18])[CH:10]=[CH:11][CH:12]=1)\[CH3:5]

Participants

6

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 131719902HCID 131719902, compound

Product 1

HCID 88162749HCID 88162749, compoundYield 35.5%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

0.5 g of hydroxylamine hydrochloride in solution in 6 cm3 of water is added to a solution of 3 g of tert-butyl (2RS,5SR)-1-{2-[3-(3-acetylphenyl)ureido]acetyl}-5-phenylprolinate in 12 cm3 of methanol and 6 cm3 of pyridine. The reaction mixture is heated under reflux for 2 hours. After evaporation of the solvents under reduced pressure at a temperature in the vicinity of 45° C., the residue is taken up in 100 cm3 of ethyl acetate and the organic phase is washed with 3 times 50 cm3 of water, dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure. The crude product obtained is purified by chromatography on silica [eluent: dichloromethane/methanol (95/5 by volume)]. The fractions containing the expected product are combined and concentrated to dryness under reduced pressure at a temperature in the vicinity of 40° C. After recrystallization in acetonitrile, 1.1 g of tert-butyl (E)-(2RS,5SR)-1-{2-{3-[3-(1-hydroxyiminoethyl)phenyl]ureido}acetyl}-5-phenylprolinate, melting at 118° C., are obtained.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureunder reflux for 2 hours
  3. customAfter evaporation of the solvents under reduced pressure at a temperature in the vicinity of 45° C.
  4. washthe organic phase is washed with 3 times 50 cm3 of water
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure
  8. customThe crude product obtained
  9. customis purified by chromatography on silica [eluent: dichloromethane/methanol (95/5 by volume)]
  10. additionThe fractions containing the expected product
  11. concentrationconcentrated to dryness under reduced pressure at a temperature in the vicinity of 40° C
  12. customAfter recrystallization in acetonitrile

Sources & evidence

ORD record
ord-349ed2c3bae84a629532f4f91c4b9815
Source dataset
uspto-grants-1997_03
Patent number
US05610144

Reaction notes

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