Acetic Anhydride → HCID 131725413, compound

HRID 1349028Notes

Reaction equation

HRID 1349028 reaction equation
[C:1]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:6]=[CH:5][C:4]([C:7]([N:9]2[CH2:13][C:12](=[N:14][NH2:15])[CH2:11][C@H:10]2[C:16]([NH:18][CH2:19][CH:20]([OH:27])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:17])=[O:8])=[CH:3][CH:2]=1.[C:34](OC(=O)C)(=[O:36])[CH3:35]>N1C=CC=CC=1>[C:34]([NH:15][N:14]=[C:12]1[CH2:13][N:9]([C:7]([C:4]2[CH:3]=[CH:2][C:1]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)=[CH:6][CH:5]=2)=[O:8])[C@H:10]([C:16]([NH:18][CH2:19][CH:20]([OH:27])[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[O:17])[CH2:11]1)(=[O:36])[CH3:35]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 131725412HCID 131725412, compound

Product 1

HCID 131725413HCID 131725413, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A hydrazono pyrrolidine derivative obtained by the general method outlined in Example 17, e.g. (2S,4EZ)-1-([1,1′-biphenyl]-4-ylcarbonyl)-4-hydrazono-N-[(2RS)-2-hydroxy-2-phenylethyl]-2-pyrrolidinecarboxamide (51 mg, 0.11 mmol) was dissolved in pyridine (1 mL). Acetic anhydride (3 eq, 32 μl, 0.35 mmol) was added, and the mixture was stirred overnight. The solvent was evaporated and the resultant crude reaction mixture was purified by column chromatography using DCM/MeOH (20:1) to collect the desired product, e.g. (2S,4EZ)-4-(acetylhydrazono)-1-([1,1′-biphenyl]-4-ylcarbonyl)-N-[(2RS)-2-hydroxy-2-phenylethyl]-2-pyrrolidinecarboxamide as a mixture of two isomers as a colorless solid in 73% yield (98.4% purity by HPLC).

Workup

  1. customThe solvent was evaporated
  2. customthe resultant crude reaction mixture
  3. customwas purified by column chromatography
  4. customto collect the desired product, e.g. (2S,4EZ)-4-(acetylhydrazono)-1-([1,1′-biphenyl]-4-ylcarbonyl)-N-[(2RS)-2-hydroxy-2-phenylethyl]-2-pyrrolidinecarboxamide
  5. additionas a mixture of two isomers as a colorless solid in 73% yield (98.4% purity by HPLC)

Sources & evidence

ORD record
ord-f61c3f2389154e92938b4e57ac938e9e
Source dataset
uspto-grants-2007_05
Patent number
US07211601B2

Reaction notes

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