Hydroxylamine → HCID 86596243, compound

HRID 459101Notes

Reaction equation

HRID 459101 reaction equation
[F:1][C:2]1[CH:34]=[CH:33][C:5]([C:6]([C:8]2[CH:32]=[CH:31][C:11]([O:12][CH2:13][CH2:14][CH2:15][C:16]#[C:17][C:18]3[CH:23]=[CH:22][C:21]([CH2:24][C@H:25]([O:29][CH3:30])[C:26]([OH:28])=[O:27])=[CH:20][CH:19]=3)=[CH:10][CH:9]=2)=O)=[CH:4][CH:3]=1.[NH2:35][OH:36]>C(O)C>[F:1][C:2]1[CH:34]=[CH:33][C:5]([C:6](=[N:35][OH:36])[C:8]2[CH:32]=[CH:31][C:11]([O:12][CH2:13][CH2:14][CH2:15][C:16]#[C:17][C:18]3[CH:23]=[CH:22][C:21]([CH2:24][C@H:25]([O:29][CH3:30])[C:26]([OH:28])=[O:27])=[CH:20][CH:19]=3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 58822672HCID 58822672, compound

Product 1

HCID 86596243HCID 86596243, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(2S)-3-(4-{5-[4-(4-Fluoro-benzoyl)-phenoxy]-pent-1-ynyl}-phenyl)-2-methoxy-propionic acid from Example 25 (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 C28H26FNO5 [M+H]+: 476.2, [M−H]−: 474.2.

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-c520591de2714eaba8e4f1ef41da0074
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Reaction notes

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