Trifluoroacetic acid → HCID 76022069, compound

HRID 1807303Notes

Reaction equation

HRID 1807303 reaction equation
[Cl:1][C:2]1[C:3]([F:45])=[C:4]([C@@H:8]2[C@:12]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=3[F:22])([C:13]#[N:14])[C@H:11]([CH2:23][C:24]([CH3:27])([CH3:26])[CH3:25])[NH:10][C@H:9]2[C:28]([NH:30][C:31]2([CH3:44])[CH2:36][CH2:35][N:34](C(OC(C)(C)C)=O)[CH2:33][CH2:32]2)=[O:29])[CH:5]=[CH:6][CH:7]=1.FC(F)(F)C(O)=O>ClCCl>[CH3:44][C:31]1([NH:30][C:28]([CH:9]2[CH:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=3[F:45])[C:12]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=3[F:22])([C:13]#[N:14])[CH:11]([CH2:23][C:24]([CH3:27])([CH3:26])[CH3:25])[NH:10]2)=[O:29])[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 53358115HCID 53358115, compound

Product 1

HCID 76022069HCID 76022069, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of racemic tert-butyl 4-((2R,3S,4R,5S)-3-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-fluorophenyl)-4-cyano-5-neopentylpyrrolidine-2-carboxamido)-4-methylpiperidine-1-carboxylate (27.0 mg, 0.0407 mmol, example 386) in dichloromethane (3 mL) was added TRIFLUOROACETIC ACID (4.44 g, 3 mL) and the reaction mixture was stirred at 0˜5 C for 2.5 hrs. The solvent was removed in vacuum and residue was dissolved in CH2Cl2 (80 mL), washed with sat Na2CO3 (15 mL), water (2×15 mL) and evaporated to give rac-(2R,3S,4R,5S)-4-(4-Chloro-2-fluoro-phenyl)-3-(3-chloro-2-fluoro-phenyl)-4-cyano-5-(2,2-dimethyl-propyl)-pyrrolidine-2-carboxylic acid (4-methyl-piperidin-4-yl)-amide as a white solid. MS (ES+) m/z Calcd: [(M+H)+]: 563. found: 563.

Workup

  1. customThe solvent was removed in vacuum and residue
  2. dissolutionwas dissolved in CH2Cl2 (80 mL)
  3. washwashed with sat Na2CO3 (15 mL), water (2×15 mL)
  4. customevaporated

Sources & evidence

ORD record
ord-966b66e378c34106a6b630a783ef09dd
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

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