Hydrochloric Acid → HCID 53358453, compound

HRID 1807305Notes

Reaction equation

HRID 1807305 reaction equation
[Cl:1][C:2]1[C:3]([F:46])=[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[CH2:41][CH2:40][CH2:39][CH:38]3[C:42]([O:44]C)=[O:43])=[CH:33][CH:32]=2)=[O:29])[CH:5]=[CH:6][CH:7]=1.O.[OH-].[Li+].Cl>C1COCC1.O.CCOC(C)=O>[Cl:1][C:2]1[C:3]([F:46])=[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])([CH3:25])[CH3:26])[NH:10][C@H:9]2[C:28]([NH:30][C:31]2[CH:32]=[CH:33][C:34]([N:37]3[CH2:41][CH2:40][CH2:39][CH:38]3[C:42]([OH:44])=[O:43])=[CH:35][CH:36]=2)=[O:29])[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 53358231HCID 53358231, compound

Product 1

HCID 53358453HCID 53358453, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 1-(4-((2R,3S,4R,5S)-3-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-fluorophenyl)-4-cyano-5-neopentylpyrrolidine-2-carboxamido)phenyl)pyrrolidine-2-carboxylate (61.2 mg, 0.091.4 mmol, example 11) in THF (4.00 ml) was added a solution of LITHIUM HYDROXIDE monohydrate (22.6 mg, 0.539 mmol) in Water (2.00 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)-3-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-fluorophenyl)-4-cyano-5-neopentylpyrrolidine-2-carboxamido)phenyl)pyrrolidine-2-carboxylic acid as a white solid. MS (ES+) m/z Calcd: [(M+H)+]: 655. found: 655.

Workup

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

Sources & evidence

ORD record
ord-cbe84b72b2ac462699334561c0dc4aea
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

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