Hydrochloric Acid → 2-[3-[4-(2-naphthamido)benzyl]-2-ethyl-1H-indol-1-yl]acetic acid

HRID 589358Notes

Reaction equation

HRID 589358 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([NH:13][C:14]1[CH:37]=[CH:36][C:17]([CH2:18][C:19]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[N:21]([CH2:28][C:29]([O:31]CC)=[O:30])[C:20]=2[CH2:34][CH3:35])=[CH:16][CH:15]=1)=[O:12].O.[OH-].[Li+].O1CCCC1.Cl>O>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([NH:13][C:14]1[CH:15]=[CH:16][C:17]([CH2:18][C:19]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[N:21]([CH2:28][C:29]([OH:31])=[O:30])[C:20]=2[CH2:34][CH3:35])=[CH:36][CH:37]=1)=[O:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 89590278ethyl 2-[3-[4-(2-naphthamido)benzyl]-2-ethyl-1H-indol-1-yl]acetate

Product 1

HCID 715717142-[3-[4-(2-naphthamido)benzyl]-2-ethyl-1H-indol-1-yl]acetic acidYield 75.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Into a dry reaction vessel, ethyl 2-[3-[4-(2-naphthamido)benzyl]-2-ethyl-1H-indol-1-yl]acetate (340 mg, 0.69 mmol), lithium hydroxide monohydrate (117 mg, 2.79 mmol), 5 mL tetrahydrofuran, 5 mL water were weighed, and stirred at room temperature for 2 h. The reaction was monitored to be complete by TLC, the system was added 10 mL water, and adjusted to pH=5 with 2 N HCl solution. A solid precipitated, it was pumping filtered, washed with dichloromethane to obtain the product as a light yellow solid 240 mg, at a yield of 75.2%.

Workup

  1. customA solid precipitated
  2. filtrationit was pumping filtered
  3. washwashed with dichloromethane

Sources & evidence

ORD record
ord-b5f166ca5e044c97998f0913f39af218
Source dataset
uspto-grants-2016_01
Patent number
US09233098B2

Reaction notes

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