(2R,4R)-2-[2-Fluoro-4-(3-methyl-pyrazol-1-yl)-phenylcarbamoyl]-4-methoxy-pyrrolidine-1-carboxylic acid tert-butyl ester → (2R,4R)-4-Methoxy-pyrrolidine-2-carboxylic acid [2-fluoro-4-(3-methyl-pyrazol-1-yl)-phenyl]-amide

HRID 2217575Notes

Reaction equation

HRID 2217575 reaction equation
C(OC([N:8]1[CH2:12][C@H:11]([O:13][CH3:14])[CH2:10][C@@H:9]1[C:15](=[O:30])[NH:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]2[CH:27]=[CH:26][C:25]([CH3:28])=[N:24]2)=[CH:19][C:18]=1[F:29])=O)(C)(C)C>C(O)(C(F)(F)F)=O.ClCCl>[F:29][C:18]1[CH:19]=[C:20]([N:23]2[CH:27]=[CH:26][C:25]([CH3:28])=[N:24]2)[CH:21]=[CH:22][C:17]=1[NH:16][C:15]([C@H:9]1[CH2:10][C@@H:11]([O:13][CH3:14])[CH2:12][NH:8]1)=[O:30]

Participants

4

Reactant 1

HCID 68805326(2R,4R)-2-[2-Fluoro-4-(3-methyl-pyrazol-1-yl)-phenylcarbamoyl]-4-methoxy-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 69737392(2R,4R)-4-Methoxy-pyrrolidine-2-carboxylic acid [2-fluoro-4-(3-methyl-pyrazol-1-yl)-phenyl]-amideYield 99.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

Boc-amine 3 (˜0.6 g, 1.427 mmol) was dissolved in 25% TFA in dichloromethane. The mixture was stirred at ambient temperature for 2 h. The solvents were removed and the residue dried under vacuum to give 4 as a tan oil (˜0.450 g).

Workup

  1. customThe solvents were removed
  2. customthe residue dried under vacuum

Sources & evidence

ORD record
ord-48f21f23ae1c4b0bb2478adc27ba864a
Source dataset
uspto-grants-2008_08
Patent number
US07407974B2

Reaction notes

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