Lithium hydroxide, monohydrate → HCID 21460787, compound

HRID 2082482Notes

Reaction equation

HRID 2082482 reaction equation
C([O:4][C:5]1[CH:28]=[CH:27][CH:26]=[CH:25][C:6]=1[C:7](=[O:24])[CH2:8][NH:9][C:10]1[C:18]2[C:13](=[CH:14][C:15]([Cl:19])=[CH:16][CH:17]=2)[NH:12][C:11]=1[C:20]([O:22]C)=[O:21])(=O)C.O.[OH-].[Li+]>O1CCCC1.O.C(OCC)(=O)C.O>[OH:4][C:5]1[CH:28]=[CH:27][CH:26]=[CH:25][C:6]=1[C:7](=[O:24])[CH2:8][NH:9][C:10]1[C:18]2[C:13](=[CH:14][C:15]([Cl:19])=[CH:16][CH:17]=2)[NH:12][C:11]=1[C:20]([OH:22])=[O:21]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 21460728HCID 21460728, compound

Product 1

HCID 21460787HCID 21460787, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 21881883Oxolane--water (1/1)SolventHCID 22728543Water ethylacetateSolvent

Conditions

Temperature
60 °C

Procedure

Dissolve 3-[(2-acetoxyphenacyl)amino]-2-carbmethoxy-6-chloroindole (800 mg, 2.15 mmol) in tetrahydrofuran/water (20 mL, 1/1). Add lithium hydroxide monohydrate (932 mg, 8.5 mmol). Seal the flask and warm to 60° C. for 3 hours. Dilute with ethyl acetate/water, acidify and separate the organic phase. Dry, precipitate with hexane and filter the solid to give the title compound (358 mg, 50%); mp 198°-200° C.

Workup

  1. customSeal the flask
  2. customseparate the organic phase
  3. customDry
  4. filtrationprecipitate with hexane and filter the solid

Sources & evidence

ORD record
ord-eb9bfd6dce8c4c8f8e4ff4002afed3b5
Source dataset
uspto-grants-1993_02
Patent number
US05189054

Reaction notes

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