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Sodium Hydroxide → HCID 21995280, compound

HRID 619368
Notes
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Reaction equation

HRID 619368 reaction equation
C([O:3][C:4]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]2[CH:19]=[CH:18][N:17]=[C:16]([NH:20][C:21]3[CH:26]=[C:25]([O:27][CH3:28])[C:24]([O:29][CH3:30])=[C:23]([O:31][CH3:32])[CH:22]=3)[N:15]=2)=[CH:9][CH:8]=1)=[O:5])C.[OH-].[Na+]>C(O)C>[C:4]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]([NH:13][C:14]2[CH:19]=[CH:18][N:17]=[C:16]([NH:20][C:21]3[CH:22]=[C:23]([O:31][CH3:32])[C:24]([O:29][CH3:30])=[C:25]([O:27][CH3:28])[CH:26]=3)[N:15]=2)=[CH:11][CH:12]=1)([OH:5])=[O:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21995173HCID 21995173, compound

Product 1

HCID 21995280HCID 21995280, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

The compound of Example 103 (250 mg, 0.57 mmol) in a solution of ethanol (10 ml) containing 6N aqueous NaOH (2.0 ml) was heated a reflux for 2 h. On cooling the ethanol was removed under reduced pressure and the basic solution brought to pH 5 with 2M hydrochloric acid. The resulting solution was concentrated under reduced pressure, and the residue taken up in hot ethanol (20 ml). This solution was filtered and the filtrate evaporated under reduced pressure to give a residue which was crystalised from ethanol to give the title compound (89 mg) as a white solid m.p. 144-150°. MS m/z 411 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperaturea reflux for 2 h
  3. customwas removed under reduced pressure
  4. concentrationThe resulting solution was concentrated under reduced pressure
  5. filtrationThis solution was filtered
  6. customthe filtrate evaporated under reduced pressure
  7. customto give a residue which
  8. customwas crystalised from ethanol

Sources & evidence

ORD record
ord-5a06928a3077488c877b904ee226afb2
Source dataset
uspto-grants-1999_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05958935

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes