Hydroxyamine hydrochloride → HCID 178451242, compound

HRID 923598Notes

Reaction equation

HRID 923598 reaction equation
[C:1]([C:3]1[CH:29]=[CH:28][C:6]([CH2:7][N:8]([CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:9](=[O:19])[C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=2)=[CH:5][CH:4]=1)#[N:2].Cl.[NH2:31][OH:32].C([O-])(O)=O.[Na+]>CN(C=O)C>[OH:32][NH:31][C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]([CH2:20][C:21]([O:23][C:24]([CH3:25])([CH3:26])[CH3:27])=[O:22])[C:9](=[O:19])[C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=2)=[CH:28][CH:29]=1)=[NH:2]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 71076902tert-butyl 2-(N-(4-cyanobenzyl)-4-nitrobenzamido)acetate

Product 1

HCID 178451242HCID 178451242, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Prepared using General Procedure 19. To a stirred solution of tert-butyl 2-(N-(4-cyanobenzyl)-4-nitrobenzamido)acetate INT-56 (11.5 g, 29.2 mmol) and TEA (10.2 mL, 73.0 mmol) in DMF (50 mL) was added hydroxylamine hydrochloride (5.07 g, 73.0 mmol). After 24 h the reaction mixture was poured onto water (200 mL) and NaHCO3 (200 mL) and extracted into EA (2×250 mL). The organics were washed with brine (3×200 mL), dried over MgSO4 and concentrated in vacuo, evaporating from hexanes, to provide 12.1 g (97%) of tert-butyl 2-(N-(4-(N-hydroxycarbamimidoyl)benzyl)-4-nitrobenzamido)acetate INT-57 as an off-white powder. LCMS-ESI (m/z) calculated for C21H24N4O6: 428; found 429 [M+H]+, tR=1.42 min (Method 10).

Workup

  1. customPrepared
  2. extractionextracted into EA (2×250 mL)
  3. washThe organics were washed with brine (3×200 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customevaporating from hexanes

Sources & evidence

ORD record
ord-72f5274fd7ab4abc8d961f0a4bc3120b
Source dataset
uspto-grants-2016_03
Patent number
US09278910B2

Reaction notes

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