Hydrochloric Acid → HCID 178512665, compound

HRID 2289750Notes

Reaction equation

HRID 2289750 reaction equation
[OH-].[Na+].C([O:5][C:6](=[O:31])[C:7]1([CH2:30][CH2:29][CH2:28][CH2:27]1)[NH:8][S:9]([C:12]1[CH:21]=[C:20]2[C:15]([C:16]([Cl:26])=[CH:17][N:18]=[C:19]2[NH:22][C:23]([NH2:25])=[NH:24])=[CH:14][CH:13]=1)(=[O:11])=[O:10])C.Cl>CO>[Cl:26][C:16]1[C:15]2[C:20](=[CH:21][C:12]([S:9]([NH:8][C:7]3([C:6]([OH:31])=[O:5])[CH2:30][CH2:29][CH2:28][CH2:27]3)(=[O:10])=[O:11])=[CH:13][CH:14]=2)[C:19]([NH:22][C:23]([NH2:25])=[NH:24])=[N:18][CH:17]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178470523HCID 178470523, compound

Product 1

HCID 178512665HCID 178512665, compoundYield 97.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
45 °C

Procedure

A solution of NaOH (75 mL, 2 M, 150 mmol) was added to a solution of N-[(4-chloro-1-guanidino-7-isoquinolinyl)sulphonyl]cycloleucine ethyl ester (1.39 g, 3.16 mmol) in MeOH (75 mL) and the mixture heated at 40-50° C. for 24 h. The cooled mixture was neutrilised with dilute HCl (75 mL, 2 M) to give a precipitate and the MeOH was evaporated in vacuo. The solid was collected by filtration, with copious water washing, and dried under high vacuum to give N-[(4-chloro-1-guanidino-7-isoquinolinyl)sulphonyl]cycloleucine (1.27 g, 3.08 mmol) as a white powder.

Workup

  1. customto give a precipitate
  2. customthe MeOH was evaporated in vacuo
  3. filtrationThe solid was collected by filtration, with copious water washing
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-38fec2518b8e433f9bb68cafa9dbd575
Source dataset
uspto-grants-2000_07
Patent number
US06093731

Reaction notes

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