Hydrochloric Acid → HCID 53358113, compound

HRID 1807299Notes

Reaction equation

HRID 1807299 reaction equation
[Cl:1][C:2]1[C:3]([F:48])=[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[CH:36]=[CH:35][C:34]([N:37]3[CH2:42][CH2:41][CH:40]([C:43]([O:45]CC)=[O:44])[CH2:39][CH2:38]3)=[CH:33][CH:32]=2)=[O:29])[CH:5]=[CH:6][CH:7]=1.O.[OH-].[Li+].Cl>C1COCC1.O.CCOC(C)=O>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([C@@:12]2([C:13]#[N:14])[C@H:11]([CH2:23][C:24]([CH3:27])([CH3:26])[CH3:25])[NH:10][C@@H:9]([C:28]([NH:30][C:31]3[CH:36]=[CH:35][C:34]([N:37]4[CH2:42][CH2:41][CH:40]([C:43]([OH:45])=[O:44])[CH2:39][CH2:38]4)=[CH:33][CH:32]=3)=[O:29])[C@@H:8]2[C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=2[F:48])=[C:16]([F:22])[CH:17]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 53358112HCID 53358112, compound

Product 1

HCID 53358113HCID 53358113, compoundYield 105.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl 1-(4-((2R,3S,4R,5S)-3-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-fluorophenyl)-4-cyano-5-neopentylpyrrolidine-2-carboxamido)phenyl)piperidine-4-carboxylate (75 mg, 0.108 mmol) in THF (4 mL) was added a solution of LITHIUM HYDROXIDE monohydrate (19.2 mg, 0.458 mmol) in Water (2 mL) dropwise. The reaction mixture was stirred at rt for 2 hrs before it was neutralized with 1N HCl. it was then diluted with EtOAc, washed with water (2×10 mL), brine (2×10 mL), dried and evaporated to give 1-(4-{[(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-carbonyl]-amino}-phenyl)-piperidine-4-carboxylic acid as a white solid (76 mg, 100%). MS (ES+) m/z Calcd: [(M+H)+]: 669. found: 669.

Workup

  1. washwashed with water (2×10 mL), brine (2×10 mL)
  2. customdried
  3. customevaporated

Sources & evidence

ORD record
ord-535873b6c6474016b1446e070306725a
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

Loading…