Acetic Anhydride → HCID 131725413, compound

HRID 1745029Notes

Reaction equation

HRID 1745029 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]-4ylcarbonyl)-4-hydrazono-N-[(2RS)-2-hydroxy-2-phenylethyl]-2-pyrrolidinecarboxamide (51 mg, 0.111 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-1df5b2ea11fa470da9db550099df3015
Source dataset
uspto-grants-2006_03
Patent number
US07018988B2

Reaction notes

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