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Water → HCID 17820131, compound

HRID 987488
Notes
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Reaction equation

HRID 987488 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N:12]1[CH:16]=[C:15]([CH2:17][O:18][C:19](=[O:27])[NH:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:14]=[CH:13]1)[N:8]=[C:7]([C:28]([O:30]CC)=[O:29])[C:6](=[O:33])[NH:5]2.[OH-].[Li+].O>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N:12]1[CH:16]=[C:15]([CH2:17][O:18][C:19](=[O:27])[NH:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:14]=[CH:13]1)[N:8]=[C:7]([C:28]([OH:30])=[O:29])[C:6](=[O:33])[NH:5]2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962Water2×HCID 3939Lithium HydroxideHCID 18008921HCID 18008921, compound

Product 1

HCID 17820131HCID 17820131, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of the compound (76.0 mg, 162 μmol) of Example 42 in ethanol. (2 ml) were added 1 mol/L aqueous solution of lithium hydroxide (567 μl, 567 μmol) and water (1 ml), and the mixture was stirred for 75 minutes at 50° C. After cooling, water was added to the reaction mixture and the insolubles were filtered off. The filtrate was brought to pH4 with 3 mol/L hydrochloric acid. The precipitated crystals were collected by filtration, washed with water, and then air-dried, thereby obtaining 27.5 mg of title compound as light brown powder. Yield 39%.

Workup

  1. temperatureAfter cooling
  2. filtrationthe insolubles were filtered off
  3. filtrationThe precipitated crystals were collected by filtration
  4. washwashed with water
  5. customair-dried

Sources & evidence

ORD record
ord-c3dd2737ef5142b9af0a70c4f0e01b88
Source dataset
uspto-grants-2003_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06632813B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes