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Hydrochloric Acid → HCID 22909006, compound

HRID 1378989
Notes
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Reaction equation

HRID 1378989 reaction equation
C[O:2][C:3]([C:5]1[CH:28]=[CH:27][C:8](/[CH:9]=[CH:10]/[C:11]2[N:19]([CH3:20])[C:18]3[C:17](=[O:21])[N:16]([CH2:22][CH3:23])[C:15](=[O:24])[N:14]([CH2:25][CH3:26])[C:13]=3[N:12]=2)=[C:7]([O:29][CH3:30])[CH:6]=1)=[O:4].O1CCCC1.O.[OH-].[Li+].Cl>O.C(O)C>[CH2:22]([N:16]1[C:17](=[O:21])[C:18]2[N:19]([CH3:20])[C:11](/[CH:10]=[CH:9]/[C:8]3[CH:27]=[CH:28][C:5]([C:3]([OH:4])=[O:2])=[CH:6][C:7]=3[O:29][CH3:30])=[N:12][C:13]=2[N:14]([CH2:25][CH3:26])[C:15]1=[O:24])[CH3:23]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 70046683HCID 70046683, compound

Product 1

HCID 22909006HCID 22909006, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 702
Ethanol
Solvent
HCID 962WaterSolvent

Procedure

Compound 20 (108 mg, 0.262 mmol) obtained in Example 19 was suspended in a solvent mixture of 2 ml of tetrahydrofuran, 2 ml of ethanol, and 1 ml of water. To the suspension was added 55 mg (1.311 mmol) of lithium hydroxide monohydrate, and the resulting mixture was stirred at room temperature for 12 hours. The reaction mixture was acidified with 2N HCl, and the precipitated crystals were collected by filtration. The obtained crude crystals were purified by column chromatography (eluent: chloroform/methanol/acetic acid=40/1/1) to give 25 mg (yield 24%) of Compound 22, which was further recrystallized from isopropanol to give a yellow powder.

Workup

  1. filtrationthe precipitated crystals were collected by filtration
  2. customThe obtained crude crystals
  3. customwere purified by column chromatography (eluent: chloroform/methanol/acetic acid=40/1/1)

Sources & evidence

ORD record
ord-d7a9405e03f7434db2cd53eff0932f50
Source dataset
uspto-grants-1997_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05670498

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes