Hydroxylamine → HCID 59015147, compound

HRID 459115Notes

Reaction equation

HRID 459115 reaction equation
[C:1]1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:6]=[CH:5][C:4]([O:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([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)=O)=[CH:3][CH:2]=1.[NH2:33][OH:34]>C(O)C>[C:1]1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:6]=[CH:5][C:4]([O:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([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)=[N:33][OH:34])=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 10296468HCID 10296468, compound

Product 1

HCID 59015147HCID 59015147, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(2S)-3-{4-[5-(Biphenyl-4-yloxy)-pentanoyl]-phenyl}-2-methoxy-propionic acid from Example 52, (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 C27H29NO5 [M+H]+: 448.2.2, [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-c5650c807235438f9548da213b8515b8
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Reaction notes

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