Hydroxylamine → tert-butyl 2-(2-(tert-butyldimethylsilyloxy)-1-(4-(N'-hydroxycarbamimidoyl)phenyl)ethylamino)acetate

HRID 572578Notes

Reaction equation

HRID 572578 reaction equation
[Si:1]([O:8][CH2:9][CH:10]([NH:19][CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:11]1[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[NH2:28][OH:29]>C(O)C>[Si:1]([O:8][CH2:9][CH:10]([NH:19][CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:11]1[CH:12]=[CH:13][C:14]([C:17](=[N:28][OH:29])[NH2:18])=[CH:15][CH:16]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 66652772Tert-butyl 2-(2-(tert-butyldimethylsilyloxy)-1-(4-cyanophenyl)ethylamino)acetate

Product 1

HCID 86683835tert-butyl 2-(2-(tert-butyldimethylsilyloxy)-1-(4-(N'-hydroxycarbamimidoyl)phenyl)ethylamino)acetateYield 105.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of tert-butyl 2-(2-(tert-butyldimethylsilyloxy)-1-(4-cyanophenyl)ethylamino)acetate (0.496 g; 1.27 mmol) and 50% aqueous hydroxylamine (0.389 mL; 6.49 mmol) in ethanol (5 mL) was heated at 70° C. for 18 hours. The solvent was evaporated in vacuo. The residue was partitioned between DCM and water. The organic phase was poured through a hydrophobic frit and evaporated in vacuo to afford the title compound (0.566 g, 100%). 1H NMR (CDCl3, 400 MHz) δ 7.59 (d, J=8.4 Hz, 2H), 7.39 (d, J=8.0 Hz, 2H), 7.00 (br s, 1H), 4.84 (br s, 2H), 3.84-3.81 (m, 1H), 3.68-3.57 (m, 2H), 3.25 (d, J=17.2 Hz, 1H), 3.08 (d, J=16.8 Hz, 1H), 2.60 (br s, 1H), 1.44 (s, 9H), 0.88 (s, 9H), 0.03 (s, 3H), 0.01 (s, 3H).

Workup

  1. customThe solvent was evaporated in vacuo
  2. customThe residue was partitioned between DCM and water
  3. additionThe organic phase was poured through a hydrophobic frit
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-174be4fed6be4d8f931beaa13ad0b25d
Source dataset
uspto-grants-2015_05
Patent number
US09029405B2

Reaction notes

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