Hydroxyamine hydrochloride → HCID 87693991, compound

HRID 2251571Notes

Reaction equation

HRID 2251571 reaction equation
[C:1]([N:3]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[N:29]=[C:30]([CH:33]3[CH2:35][CH2:34]3)[O:31][CH:32]=2)=[CH:24][CH:23]=1)[CH2:4][CH2:5][C:6]1[CH:20]=[CH:19][C:9]([O:10][C:11]([CH3:18])([CH3:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:8][CH:7]=1)#[N:2].Cl.[NH2:37][OH:38].C([O-])(=O)C.[Na+]>CN(C=O)C>[NH2:2]/[C:1](/[N:3]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[N:29]=[C:30]([CH:33]3[CH2:34][CH2:35]3)[O:31][CH:32]=2)=[CH:24][CH:23]=1)[CH2:4][CH2:5][C:6]1[CH:20]=[CH:19][C:9]([O:10][C:11]([CH3:17])([CH3:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:8][CH:7]=1)=[N:37]\[OH:38]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 86598933HCID 86598933, compound

Product 1

HCID 87693991HCID 87693991, compoundYield 113.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl 2-[4-(2-{cyano[4-(2-cyclopropyl-1,3-oxazol-4-yl)benzyl]amino}ethyl)phenoxy]-2-methylpropanoate (0.38 g, 0.80 mmol) in DMF (2 ml) was added hydroxylamine hydrochloride (0.20 g, 2.94 mmol) followed by sodium acetate (2.88 g, 3.59 mmol). The mixture was stirred at rt for 12 h. The reaction mixture was partitioned between EtOAc and water. The aqueous phase was extracted with EtOAc (2×20 ml). The combined organic phases were washed with brine, dried with MgSO4, and concentrated in vacuo to yield ethyl 2-[4-(2-{[(E)-amino(hydroxyimino)methyl][4-(2-cyclopropyl-1,3-oxazol-4-yl)benzyl]amino}ethyl)phenoxy]-2-methylpropanoate (0.46 g) which was used directly without purification.

Workup

  1. customThe reaction mixture was partitioned between EtOAc and water
  2. extractionThe aqueous phase was extracted with EtOAc (2×20 ml)
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5fc2abe925e54a6ea6c9fd7c5b811b1e
Source dataset
uspto-grants-2008_01
Patent number
US07319104B2

Reaction notes

Loading…