Hydrochloric Acid → 3-[(1-Cyano-4-hydroxy-7-phenethyl-isoquinoline-3-carbonyl)-amino]-2,2-dimethyl-propionic acid

HRID 1481138Notes

Reaction equation

HRID 1481138 reaction equation
C[O:2][C:3](=[O:32])[C:4]([CH3:31])([CH3:30])[CH2:5][NH:6][C:7]([C:9]1[N:10]=[C:11]([C:28]#[N:29])[C:12]2[C:17]([C:18]=1[OH:19])=[CH:16][CH:15]=[C:14]([CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH:13]=2)=[O:8].[OH-].[Na+].Cl>CO>[C:28]([C:11]1[C:12]2[C:17](=[CH:16][CH:15]=[C:14]([CH2:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:13]=2)[C:18]([OH:19])=[C:9]([C:7]([NH:6][CH2:5][C:4]([CH3:31])([CH3:30])[C:3]([OH:32])=[O:2])=[O:8])[N:10]=1)#[N:29]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 898130143-[(1-Cyano-4-hydroxy-7-phenethyl-isoquinoline-3-carbonyl)-amino]-2,2-dimethyl-propionic acid methyl ester

Product 1

HCID 717359453-[(1-Cyano-4-hydroxy-7-phenethyl-isoquinoline-3-carbonyl)-amino]-2,2-dimethyl-propionic acidYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3-[(1-cyano-4-hydroxy-7-phenethyl-isoquinoline-3-carbonyl)-amino]-2,2-dimethyl-propionic acid methyl ester (55 mg, 0.13 mmol), 2 M NaOH (2 mL) and MeOH (2 mL) was stirred at r.t. for 3 h. 1 M HCl was added until pH was ˜2, and the resulting suspension was extracted with EtOAc. The organic layer was dried over MgSO4 and concentrated. The crude product was purified by column chromatography (0-30% EtOAc/hexanes+2% AcOH) to give 38 mg of the title compound. MS: (−) m/z 416.14 (M−1).

Workup

  1. extractionthe resulting suspension was extracted with EtOAc
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated
  4. customThe crude product was purified by column chromatography (0-30% EtOAc/hexanes+2% AcOH)

Sources & evidence

ORD record
ord-3b969af328634b3ba330d01803a61fe6
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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