Hydroxyamine hydrochloride → HCID 178456097, compound

HRID 1455582Notes

Reaction equation

HRID 1455582 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) is 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 is partitioned between ethyl acetate and water. The organic layer is separated, dried over magnesium sulfate and then evaporated under reduced pressure. The residual oil is 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 a solid. MS: MH+248.

Workup

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

Sources & evidence

ORD record
ord-dcf6bfaf3999417d8457d22b1df87010
Source dataset
uspto-grants-2009_01
Patent number
US07482448B2

Reaction notes

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