Sodium Hydroxide → HCID 68284185, compound

HRID 1527247Notes

Reaction equation

HRID 1527247 reaction equation
C[O:2][C:3](=[O:29])[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([CH2:14][O:15][Si:16]([CH:23]([CH3:25])[CH3:24])([CH:20]([CH3:22])[CH3:21])[CH:17]([CH3:19])[CH3:18])=[CH:11][CH:12]=2)[C:7]([C:26](=[O:28])[CH3:27])=[CH:6]1.[OH-].[Na+]>C1COCC1.O>[C:26]([C:7]1[C:8]2[C:13](=[CH:12][CH:11]=[C:10]([CH2:14][O:15][Si:16]([CH:23]([CH3:25])[CH3:24])([CH:17]([CH3:18])[CH3:19])[CH:20]([CH3:21])[CH3:22])[CH:9]=2)[N:5]([CH2:4][C:3]([OH:29])=[O:2])[CH:6]=1)(=[O:28])[CH3:27]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68283544HCID 68283544, compound

Product 1

HCID 68284185HCID 68284185, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (3-acetyl-5-triisopropylsilanyloxymethyl-indol-1-yl)-acetic acid methyl ester (109 mg, 0.138 mmol) in THF (5 mL) and water (0.5 mL) was added 1N NaOH (0.69 mL, 0.69 mmol), and stirring was continued at RT for 16 h. The reaction mixture was partitioned between EtOAc and saturated aqueous NaHCO3. The aqueous layer was extracted with EtOAC (2×), the combined organics were dried (phase separator) and concentrated in vacuo to afford the title compound as a yellow wax. MS (LC/MS): 404 [M+H]+; tR (HPLC conditions k): 4.35 min.

Workup

  1. customThe reaction mixture was partitioned between EtOAc and saturated aqueous NaHCO3
  2. extractionThe aqueous layer was extracted with EtOAC (2×)
  3. customthe combined organics were dried (phase separator)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cd3f349cc88e423bbee7e4acf53a6ee4
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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