Potassium Carbonate → tert-butyl N-[(1Z,2S)-1-amino-3-cyclopropyl-1-hydroxyiminopropan-2-yl]carbamate

HRID 927414Notes

Reaction equation

HRID 927414 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl.[NH2:8][OH:9].[C:10]([C@@H:12]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:13][CH:14]1[CH2:16][CH2:15]1)#[N:11]>O.C(O)C>[NH2:11]/[C:10](=[N:8]\[OH:9])/[C@@H:12]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:21])([CH3:23])[CH3:22])[CH2:13][CH:14]1[CH2:16][CH2:15]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 71087345(S)-tert-Butyl 1-cyano-2-cyclopropylethylcarbamate

Product 1

HCID 89262365tert-butyl N-[(1Z,2S)-1-amino-3-cyclopropyl-1-hydroxyiminopropan-2-yl]carbamateYield 94%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Potassium carbonate (2.18 g, 16 mmol) was dissolved in water (8 mL) and hydroxylamine hydrochloride (1.1 g, 16 mmol) was added. A solution of (S)-tert-butyl 1-cyano-2-cyclopropylethylcarbamate (3.31 g, 16 mmol) in ethanol (24 mL) was added thereto and the resulting reaction mixture was stirred for 72 h. After evaporation of solvents, the residue was dissolved with ethyl acetate (20 mL) and then filtered. The filtrate was concentrated to yield crude product as yellow solid (3.61 g, 94%); MS (EI): m/e 244.2 [M+H]+.

Workup

  1. customthe resulting reaction mixture
  2. customAfter evaporation of solvents
  3. dissolutionthe residue was dissolved with ethyl acetate (20 mL)
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-a18fa72d740f486aa58238a437e81328
Source dataset
uspto-grants-2016_03
Patent number
US09290451B2

Reaction notes

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