Sodium Hydroxide → HCID 22636752, compound

HRID 2415787Notes

Reaction equation

HRID 2415787 reaction equation
C([O:3][C:4](=[O:30])[CH2:5][N:6]1[C:12]2[CH:13]=[C:14]([NH:17][C:18]([C:20]3[NH:21][C:22]4[C:27]([CH:28]=3)=[CH:26][C:25]([Cl:29])=[CH:24][CH:23]=4)=[O:19])[CH:15]=[CH:16][C:11]=2[O:10][CH2:9][CH2:8][CH2:7]1)C.[OH-].[Na+]>CO.C1COCC1>[Cl:29][C:25]1[CH:26]=[C:27]2[C:22](=[CH:23][CH:24]=1)[NH:21][C:20]([C:18]([NH:17][C:14]1[CH:15]=[CH:16][C:11]3[O:10][CH2:9][CH2:8][CH2:7][N:6]([CH2:5][C:4]([OH:30])=[O:3])[C:12]=3[CH:13]=1)=[O:19])=[CH:28]2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 69755749HCID 69755749, compound

Product 1

HCID 22636752HCID 22636752, compoundYield 97.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

{2-[(5-Chloro-1H-indole-2-carbonyl)-amino]-7,8-dihydro-6H-5-oxa-9-aza-benzocyclohepten-9-yl}-acetic acid ethyl ester (10 mg, 0.023 mmol, 1 eq.) was dissolved in a mixture of 1 mL of MeOH and 1 mL of THF and treated with 1 mL 1N NaOH. The reaction was stirred at room temperature for 3 hrs at which time the solvents were removed by evaporation and the residue acidified with 1N HCl. The precipitate was collected on a filter, dried and purified on preparative TLC in 9:1 CH2Cl2/MeOH to afford 9 mg of the product as a white solid. LC MS: AP+ 400/402,

Workup

  1. customwere removed by evaporation
  2. customThe precipitate was collected on a filter
  3. customdried
  4. custompurified on preparative TLC in 9:1 CH2Cl2/MeOH

Sources & evidence

ORD record
ord-196a3dd479d442b4b58bc0d025ebd4b3
Source dataset
uspto-grants-2004_11
Patent number
US06821977B2

Reaction notes

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