Hydroxylamine → HCID 86596241, compound

HRID 459089Notes

Reaction equation

HRID 459089 reaction equation
[C:1]([C:9]1[CH:31]=[CH:30][C:12]([O:13][CH2:14][C:15]#[C:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][C@H:24]([O:28][CH3:29])[C:25]([OH:27])=[O:26])=[CH:19][CH:18]=2)=[CH:11][CH:10]=1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:32][OH:33]>C(O)C>[OH:33][N:32]=[C:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:9]1[CH:31]=[CH:30][C:12]([O:13][CH2:14][C:15]#[C:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][C@H:24]([O:28][CH3:29])[C:25]([OH:27])=[O:26])=[CH:19][CH:18]=2)=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 58822702HCID 58822702, compound

Product 1

HCID 86596241HCID 86596241, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(2S)-3-{4-[3-(4-Benzoyl-phenoxy)-prop-1-ynyl]-phenyl}-2-methoxy-propionic acid (0.01 mmol, 1 eq) (Example 2) was mixed with Hydroxylamine chlorydrate (4 eq), pyrydine (10 eq) and Ethanol (2 ml) and the mixture reaction was stirred overnight. The ethanol was evaporated under vacuo and HCl 0.5% was added to the residue to pH=3. Extracted with Ethyl Acetate and concentrated to give the title product as a mixture of two oximes. MS(ES) for C26H23NO5 [M+H]+: 430.2, [M−H]−: 428.2.

Workup

  1. customthe mixture reaction
  2. customThe ethanol was evaporated under vacuo and HCl 0.5%
  3. additionwas added to the residue to pH=3
  4. extractionExtracted with Ethyl Acetate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-09a74df4a78440b981e7b4300c60b41a
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Reaction notes

Loading…