Hydroxylamine → HCID 86596244, compound

HRID 459104Notes

Reaction equation

HRID 459104 reaction equation
[C:1]([C:9]1[CH:32]=[CH:31][C:12]([O:13][CH2:14][CH2:15][C:16]#[C:17][C:18]2[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]=2)=[CH:11][CH:10]=1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:33][OH:34]>C(O)C>[OH:34][N:33]=[C:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:9]1[CH:32]=[CH:31][C:12]([O:13][CH2:14][CH2:15][C:16]#[C:17][C:18]2[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]=2)=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 10225845HCID 10225845, compound

Product 1

HCID 86596244HCID 86596244, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(2S)-3-{4-[4-(4-Benzoyl-phenoxy)-but-1-ynyl]-phenyl}-2-methoxy-propionic acid from Example 42, (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 C27H25NO5 [M+H]+: 444.2.

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-481ad7259e6642afb232dd6194dcca53
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Reaction notes

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