Hydroxyamine hydrochloride → HCID 178456097, compound

HRID 1796129Notes

Reaction equation

HRID 1796129 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][CH:8]([CH2:13][CH3:14])[CH:9]([C:11]#[N:12])[OH:10])([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:17][OH:18]>CO.C[O-].[Na+]>[C:1]([O:5][C:6](=[O:15])[NH:7][C@H:8]([CH:9]([OH:10])[C:11](=[NH:12])[NH:17][OH:18])[CH2:13][CH3:14])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 23586837(2-Cyano-1-ethyl-2-hydroxy-ethyl)-carbamic acid tert-butyl ester

Product 1

HCID 178456097HCID 178456097, compoundYield 32.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent3×HCID 10942334Sodium MethoxideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of (2-cyano-1-ethyl-2-hydroxy-ethyl)-carbamic acid tert-butyl ester (9.53 g, 44 mmol) in methanol (80 ml) was cooled to 0° C. and treated successively with hydroxylamine hydrochloride (3.05, 44 mmol) in methanol (80 ml) and 25% sodium methoxide solution in methanol (10.2 ml). Stirred at 0° C. for 5 minutes, cold bath removed and the reaction mixture stirred at room temperature for 5 hours. Methanol evaporated off under reduced pressure, crude partitioned between ethyl acetate and water. Organic layer separated, dried (MgSO4) and evaporated under reduced pressure to give yellow oil. Purified by mplc, eluting with a mixture of ethyl acetate-heptane to give the title compound as white solid (3.5 g); MS: M(H+) 248.

Workup

  1. customcold bath removed
  2. stirringthe reaction mixture stirred at room temperature for 5 hours
  3. customMethanol evaporated off under reduced pressure, crude
  4. custompartitioned between ethyl acetate and water
  5. customOrganic layer separated
  6. dry with materialdried (MgSO4)
  7. customevaporated under reduced pressure
  8. customto give yellow oil
  9. customPurified by mplc
  10. washeluting with a mixture of ethyl acetate-heptane

Sources & evidence

ORD record
ord-973c7f55f5e540ed9338ceed166b05b2
Source dataset
uspto-grants-2006_04
Patent number
US07030116B2

Reaction notes

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