Sodium Hydroxide → HCID 178524190, compound

HRID 491766Notes

Reaction equation

HRID 491766 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[O:12][C:11]([C:13]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][N:17]=3)=[O:14])=[C:10]([NH:23][C:24]([C@H:26]3[CH2:31][CH2:30][C@H:29]([N:32]4[CH2:36][CH2:35][CH2:34][C:33]4=[O:37])[CH2:28][CH2:27]3)=[O:25])[C:9]=2[CH:38]=1)=[O:4].[OH-].[Na+]>O1CCCC1CO>[C:3]([C:5]1[CH:6]=[CH:7][C:8]2[O:12][C:11]([C:13]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][N:17]=3)=[O:14])=[C:10]([NH:23][C:24]([C@H:26]3[CH2:27][CH2:28][C@H:29]([N:32]4[CH2:36][CH2:35][CH2:34][C:33]4=[O:37])[CH2:30][CH2:31]3)=[O:25])[C:9]=2[CH:38]=1)([OH:4])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178497415HCID 178497415, compound

Product 1

HCID 178524190HCID 178524190, compoundYield 94.7%

Reagents, catalysts & solvents 1

HCID 7360Tetrahydrofurfuryl alcoholSolvent

Procedure

Trans-5-methoxycarbonyl-3-[4-(2-oxopyrrolidin-1-yl)-cyclohexylcarbonylamino]-N-(5-chloropyridin-2-yl)benzofuran-2-carboxamide (710 mg) obtained in Example 1 is suspended in tetrahydrofuran-methanol (1:1, 10 ml), and thereto is added 4N aqueous sodium hydroxide solution (2 ml) under ice-cooling. The mixture is warmed to room temperature, and stirred for 18 hours. The reaction solution is concentrated under reduced pressure, and thereto is poured ice-water, and the mixture is neutralized with 10% hydrochloric acid. The precipitates are collected by filtration, washed with water, and dried to give the title compound (655 mg).

Workup

  1. temperaturecooling
  2. concentrationThe reaction solution is concentrated under reduced pressure
  3. additionis poured ice-water
  4. filtrationThe precipitates are collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-47d16fff13c043ea8e9055cea9d8b650
Source dataset
uspto-grants-2009_05
Patent number
US07531537B2

Reaction notes

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