Hydroxyamine hydrochloride → HCID 178456097, compound

HRID 1765679Notes

Reaction equation

HRID 1765679 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 g, 44 mmol) in methanol (80 ml) and 25% sodium methoxide solution in methanol (10.2 ml). After stirring at 0° C. for 5 minutes the reaction mixture stirred at room temperature for 5 hours and then evaporated. The residue was partitioned between ethyl acetate and water. The organic layer was separated, dried (MgSO4) and then evaporated under reduced pressure. The residual yellow oil was subjected to mplc, eluting with a mixture of ethyl acetate and heptane to give {(S)-1-[hydroxy-(N-hydroxycarbamimidoyl)-methyl]-propyl}-carbamic acid tert-butyl ester (3.5 g) as white solid. MS: M(H+) 248.

Workup

  1. stirringstirred at room temperature for 5 hours
  2. customevaporated
  3. customThe residue was partitioned between ethyl acetate and water
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. customevaporated under reduced pressure
  7. washeluting with a mixture of ethyl acetate and heptane

Sources & evidence

ORD record
ord-6a62b01b874c4d24ae4d0f2ac758180c
Source dataset
uspto-grants-2007_06
Patent number
US07226921B2

Reaction notes

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