Hydroxyamine hydrochloride → HCID 178501575, compound

HRID 923619Notes

Reaction equation

HRID 923619 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][CH:16]=1)[CH2:9][C:10]([O:12][CH3:13])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:24][OH:25]>CN(C=O)C.CC(=O)OCC>[C:1]([O:5][C:6]([N:8]([CH2:14][C:15]1[CH:16]=[CH:17][C:18]([C:21](=[NH:22])[NH:24][OH:25])=[CH:19][CH:20]=1)[CH2:9][C:10]([O:12][CH3:13])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 71076677Methyl 2-((tert-butoxycarbonyl)(4-cyanobenzyl)amino)acetate

Product 1

HCID 178501575HCID 178501575, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Prepared using General Procedure 19. To a stirring solution of methyl 2-((tert-butoxycarbonyl)(4-cyanobenzyl)amino)acetate INT-74 (1.35 g, 4.44 mmol) in DMF (8 mL) was added TEA (1.546 mL, 11.09 mmol) followed by hydroxylamine hydrochloride (0.771 g, 11.1 mmol). After stirring at room temperature for 48 h the reaction mixture was diluted with EA (100 mL) and the washed with brine (2×150 mL). The crude product was purified by chromatography (MeOH/DCM) to afford 1.28 g (85%) of methyl 2-((tert-butoxycarbonyl)(4-(N-hydroxycarbamimidoyl)benzyl)amino)acetate INT-75 as a viscous oil. LCMS-ESI (m/z) calculated for C16H23N3O5: 337; found 338 [M+H]+, tR=1.17 min (Method 10).

Workup

  1. customPrepared
  2. washthe washed with brine (2×150 mL)
  3. customThe crude product was purified by chromatography (MeOH/DCM)

Sources & evidence

ORD record
ord-080dd8d035ff4dac8fad29d32500f140
Source dataset
uspto-grants-2016_03
Patent number
US09278910B2

Reaction notes

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