Methanol → HCID 71571709, compound

HRID 589340Notes

Reaction equation

HRID 589340 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:36]=[CH:35][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[CH3:34])=[CH:16][CH:15]=1)=[O:12].O.[OH-].[Li+].O1CCCC1.CO>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[CH3:34])=[CH:35][CH:36]=1)=[O:12]

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 89590295ethyl 2-[3-[4-(2-naphthamido)benzyl]-2-methyl-1H-indol-1-yl]acetate

Product 1

HCID 71571709HCID 71571709, compoundYield 20.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a dry reaction vessel, ethyl 2-[3-[4-(2-naphthamido)benzyl]-2-methyl-1H-indol-1-yl]acetate (530 mg, 1.11 mmol), lithium hydroxide monohydrate (140 mg, 3.34 mmol), 5 mL tetrahydrofuran, 5 mL methanol, 10 mL water were added successively, and stirred at room temperature for 1 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. A solid precipitated, and was washed with ethyl acetate, dichloromethane, acetonitrile to obtain the product 100 mg as a white solid, at a yield of 20.1%.

Workup

  1. additionwere added successively
  2. customThe solvent was rotate evaporated
  3. customA solid precipitated
  4. washwas washed with ethyl acetate, dichloromethane, acetonitrile

Sources & evidence

ORD record
ord-007f3965e1504b78b6f5be26cdfe568c
Source dataset
uspto-grants-2016_01
Patent number
US09233098B2

Reaction notes

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