Hydroxylamine → HCID 86596240, compound

HRID 459088Notes

Reaction equation

HRID 459088 reaction equation
[F:1][C:2]1[CH:32]=[CH:31][CH:30]=[CH:29][C:3]=1[C:4]([C:6]1[CH:28]=[CH:27][C:9]([O:10][CH2:11][C:12]#[C:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][C@H:21]([O:25][CH3:26])[C:22]([OH:24])=[O:23])=[CH:16][CH:15]=2)=[CH:8][CH:7]=1)=O.[NH2:33][OH:34]>C(O)C>[F:1][C:2]1[CH:32]=[CH:31][CH:30]=[CH:29][C:3]=1[C:4](=[N:33][OH:34])[C:6]1[CH:28]=[CH:27][C:9]([O:10][CH2:11][C:12]#[C:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][C@H:21]([O:25][CH3:26])[C:22]([OH:24])=[O:23])=[CH:16][CH:15]=2)=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 58822581HCID 58822581, compound

Product 1

HCID 86596240HCID 86596240, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(2S)-3-(4-{3-[4-(2-Fluoro-benzoyl)-phenoxy]-prop-1-ynyl}-phenyl)-2-methoxy-propionic acid from Example 10, (0.01 mmol, 1 eq) 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 C26H22FNO5 [M+H]+: 448.2, [M−H]−: 446.2.

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-57ea3885ebde4899823099df9b0527c0
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Reaction notes

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