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Hydrochloric Acid → 3-{[4-Hydroxy-7-(4-methoxy-benzylamino)-isoquinoline-3-carbonyl]amino}-2,2-dimethyl-propionic acid

HRID 1481148
Notes
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Reaction equation

HRID 1481148 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([NH:12][CH2:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)=[CH:9][CH:10]=2)[CH:5]=[N:4][C:3]=1[C:22]([NH:24][CH2:25][C:26]([CH3:32])([CH3:31])[C:27]([O:29]C)=[O:28])=[O:23].O.CCOC(C)=O.Cl>CO.[OH-].[Na+]>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([NH:12][CH2:13][C:14]3[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=3)=[CH:9][CH:10]=2)[CH:5]=[N:4][C:3]=1[C:22]([NH:24][CH2:25][C:26]([CH3:32])([CH3:31])[C:27]([OH:29])=[O:28])=[O:23]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8857Ethyl AcetateHCID 89813031Methyl 3-(4-hydroxy-7-(4-methoxybenzylamino)isoquinoline-3-carboxamido)-2,2-dimethylpropanoate

Product 1

HCID 898129293-{[4-Hydroxy-7-(4-methoxy-benzylamino)-isoquinoline-3-carbonyl]amino}-2,2-dimethyl-propionic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent
HCID 14798Sodium HydroxideSolvent

Procedure

Methyl 3-(4-hydroxy-7-(4-methoxybenzylamino)isoquinoline-3-carboxamido)-2,2-dimethylpropanoate (15 mg, 0.03 mmol) was dissolved in MeOH (2 mL) and 2 N NaOH (2 mL). After stirring for 5 hours at room temperature, H2O (15 mL) and EtOAc (15 mL) were added. To the stirred mixture was added 1 N hydrochloric acid until pH was 1. The layers were separated and the aqueous layer was extracted twice with EtOAc. The combined organic layers were dried over MgSO4, concentrated, and purified by flash chromatography (0-20% MeOH/CH2Cl2) to give the title compound in 13 mg. MS: (−) m/z 422.13 (M−1).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted twice with EtOAc
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. concentrationconcentrated
  5. custompurified by flash chromatography (0-20% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-43f474aaf62c4028b23d080f5b1f4361
Source dataset
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09409892B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes