Hydrochloric Acid → HCID 11439911, compound

HRID 908819Notes

Reaction equation

HRID 908819 reaction equation
C[O:2][C:3](=[O:28])[CH2:4][NH:5][C:6]([C:8]1[N:9]=[C:10]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:11]2[C:16]([C:17]=1[O:18][C:19](=[O:21])[CH3:20])=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:7].Cl.C([O-])(O)=O.[Na+]>>[C:19]([O:18][C:17]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[N:9][C:8]=1[C:6]([NH:5][CH2:4][C:3]([OH:28])=[O:2])=[O:7])(=[O:21])[CH3:20]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 66713284HCID 66713284, compound

Product 1

HCID 11439911HCID 11439911, compoundYield 52.1%

Procedure

A mixture of [(4-Acetoxy-1-phenyl-isoquinoline-3-carbonyl)-amino]-acetic acid methyl ester (3.8 mg, 0.01 mmol) and aqueous 6N HCl (1 ml) was stirred at ambient temperature for 16 h before the pH of the solution was adjusted to ca. 8 by addition of concentrated aqueous NaHCO3 solution. The solution was washed with EtOAc (2×10 ml) before it was acidified by addition of aqueous 2N HCl. Subsequently, the mixture was extracted with EtOAc (2×10 ml). The combined organic phases were dried over MgSO4 and evaporated in vacuo to give the title compound as a yellow oil (1.9 mg); MS-(+)-ion: M+1=364.9.

Workup

  1. washThe solution was washed with EtOAc (2×10 ml) before it
  2. additionwas acidified by addition of aqueous 2N HCl
  3. extractionSubsequently, the mixture was extracted with EtOAc (2×10 ml)
  4. dry with materialThe combined organic phases were dried over MgSO4
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-ac7ff31ebe404019a92df0ee410941e4
Source dataset
uspto-grants-2011_09
Patent number
US08017625B2

Reaction notes

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