Sodium Hydroxide → HCID 10095023, compound

HRID 1916536Notes

Reaction equation

HRID 1916536 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[CH:12][C:13]([C:16]#[C:17][CH2:18][CH2:19][C:20]3[CH:35]=[CH:34][C:23]([CH2:24][N:25]4[CH2:29][CH2:28][CH2:27][CH:26]4[C:30]([O:32]C)=[O:31])=[CH:22][CH:21]=3)=[N:14][CH:15]=2)=[CH:6][CH:5]=1>CO>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[CH:12][C:13]([C:16]#[C:17][CH2:18][CH2:19][C:20]3[CH:21]=[CH:22][C:23]([CH2:24][N:25]4[CH2:29][CH2:28][CH2:27][CH:26]4[C:30]([OH:32])=[O:31])=[CH:34][CH:35]=3)=[N:14][CH:15]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69075803HCID 69075803, compound

Product 1

HCID 10095023HCID 10095023, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.5 mL 1 M NaOH solution are added to a solution of 33 mg (0.07 mmol) methyl 1-(4-{4-[5-(4-chloro-phenyl)-pyridin-2-yl]-but-3-ynyl}-benzyl)-pyrrolidine-2-carboxylate (Example 2.14) in 5 mL MeOH and the reaction mixture is stirred for 4 h at RT. The mixture is evaporated down i. vac., combined with 5 mL water, extracted with 10 mL EtOAc and the aqueous phase is saturated with NaCl, during which time the product is precipitated. It is evaporated down again i. vac., the residue is combined with EtOH, filtered and the solvent is eliminated.

Workup

  1. customThe mixture is evaporated down i
  2. extractionextracted with 10 mL EtOAc
  3. customis precipitated
  4. customIt is evaporated down again i
  5. filtrationfiltered

Sources & evidence

ORD record
ord-e8d8f1f810c74ea0b7c2883d643bbefc
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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