Hydrazine hydrate (1:1) → HCID 131725412, compound

HRID 1745028Notes

Reaction equation

HRID 1745028 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]([C:7]([N:9]2[CH2:13][C:12](=O)[CH2:11][C@H:10]2[C:15]([NH:17][CH2:18][CH:19]([OH:26])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:16])=[O:8])=[CH:3][CH:2]=1.O.[NH2:34][NH2:35]>>[C:1]1([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:6]=[CH:5][C:4]([C:7]([N:9]2[CH2:13][C:12](=[N:34][NH2:35])[CH2:11][C@H:10]2[C:15]([NH:17][CH2:18][CH:19]([OH:26])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:16])=[O:8])=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 69250404HCID 69250404, compound

Product 1

HCID 131725412HCID 131725412, compoundYield 63%

Procedure

Following the general method as outlined in Example 17, starting from (2S)-1-([1,1′-biphenyl]-4-ylcarbonyl)-N-[(2RS)-2-hydroxy-2-phenylethyl]-4-oxo-2-pyrrolidinecarboxamide and hydrazine hydrate (4% in EtOH), the resultant crude reaction mixture was purified by column chromatography using DCM/MeOH (30:1) to collect the desired product, e.g. (2S,4EZ)-1-([1,1′-biphenyl]-4-ylcarbonyl)-4-hydrazono-N-[(2RS)-2-hydroxy-2-phenylethyl]-2-pyrrolidinecarboxamide as a mixture of two isomers as a colorless solid in 63% yield (95.3% purity by HPLC).

Workup

  1. customthe resultant crude reaction mixture
  2. customwas purified by column chromatography
  3. customto collect the desired product, e.g. (2S,4EZ)-1-([1,1′-biphenyl]-4-ylcarbonyl)-4-hydrazono-N-[(2RS)-2-hydroxy-2-phenylethyl]-2-pyrrolidinecarboxamide
  4. additionas a mixture of two isomers as a colorless solid in 63% yield (95.3% purity by HPLC)

Sources & evidence

ORD record
ord-867dd4ca7c7143a9a0ce6ed8026f5f70
Source dataset
uspto-grants-2006_03
Patent number
US07018988B2

Reaction notes

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