Tetrahydrofuran → 2-[1-[4-(2-naphthamido)benzyl]-2-methyl-1H-indol-3-yl]acetic acid

HRID 589335Notes

Reaction equation

HRID 589335 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:35]=[CH:34][C:17]([CH2:18][N:19]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:21]([CH2:28][C:29]([O:31]C)=[O:30])=[C:20]2[CH3:33])=[CH:16][CH:15]=1)=[O:12].O.[OH-].[Li+].O1CCCC1>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][N:19]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:21]([CH2:28][C:29]([OH:31])=[O:30])=[C:20]2[CH3:33])=[CH:34][CH:35]=1)=[O:12]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 89590251methyl 2-[1-[4-(2-naphthamido)benzyl]-2-methyl-1H-indol-3-yl]acetate

Product 1

HCID 715734292-[1-[4-(2-naphthamido)benzyl]-2-methyl-1H-indol-3-yl]acetic acidYield 55.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a dry reaction vessel, methyl 2-[1-[4-(2-naphthamido)benzyl]-2-methyl-1H-indol-3-yl]acetate (150 mg, 0.324 mmol), lithium hydroxide monohydrate (55 mg, 1.31 mmol), 3 mL tetrahydrofuran, 3 mL water were weighed, and stirred at room temperature for 2 h. The reaction was monitored to be complete by TLC. The solvent was rotate evaporated. It was adjusted to pH=3-4 with 2 N HCl solution. It was extracted by ethyl ester, rotate evaporated to dryness to obtain the product as a white solid 80 mg. After recrystallization by ethyl acetate, a pure product 51 mg was obtained, at a yield of 35.2%.

Workup

  1. customThe solvent was rotate evaporated
  2. extractionIt was extracted by ethyl ester, rotate
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-7a61c27eeaf04124835325105b092d34
Source dataset
uspto-grants-2016_01
Patent number
US09233098B2

Reaction notes

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