Hydrochloric Acid → HCID 11585483, compound

HRID 551955Notes

Reaction equation

HRID 551955 reaction equation
[CH:1]1([CH2:6][N:7]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]#[C:28][C:29]3[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=3)=[CH:23][CH:22]=2)[C:8]2[CH:9]=[CH:10][C:11]([OH:19])=[C:12]([CH:18]=2)[C:13]([O:15]CC)=[O:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.O.[Li+].[OH-].Cl>C1COCC1>[CH:1]1([CH2:6][N:7]([CH2:20][C:21]2[CH:22]=[CH:23][C:24]([C:27]#[C:28][C:29]3[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=3)=[CH:25][CH:26]=2)[C:8]2[CH:9]=[CH:10][C:11]([OH:19])=[C:12]([CH:18]=2)[C:13]([OH:15])=[O:14])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 67170976HCID 67170976, compound

Product 1

HCID 11585483HCID 11585483, compoundYield 114.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of ethyl 5-((cyclopentylmethyl){4-[(4-methoxyphenyl)ethynyl]-benzyl}amino)-2-hydroxybenzoate (200 mg; 0.43 mmol) was dissolved in THF (4 mL) and water (1.00 mL) was added LiOH (178 mg; 4.26 mmol). The mixture was then heated in MW for 2500 s at 100° C. It was poured into a 1N solution of HCl and extracted twice with EtOAc. The combined organic layers were dried over magnesium sulfate, filtered and concentrated to give 225 mg of a yellow oil. The oil was suspended in methanol and triturated to give 140 mg (72%) of the title compound as a yellow powder. Rt: 4.08 min (purity: 99.1%), LC/MS: M+(ESI): 456.0, M−(ESI): 454.2.

Workup

  1. extractionextracted twice with EtOAc
  2. dry with materialThe combined organic layers were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f9ee95c8ab5a4944aa4fb6ab9d9a5e7f
Source dataset
uspto-grants-2011_05
Patent number
US07947851B2

Reaction notes

Loading…