Hydrochloric Acid → HCID 135710948, compound

HRID 1059929Notes

Reaction equation

HRID 1059929 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]([NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[N:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]2[C:22]([C:23]([O:25]C)=[O:24])=[CH:21][CH:20]=[CH:19][N:18]=2)[CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl>CO.O>[C:31]([O:30][C:28]([NH:27][C:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[N:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]2[C:22]([C:23]([OH:25])=[O:24])=[CH:21][CH:20]=[CH:19][N:18]=2)[CH:12]=1)=[O:29])([CH3:34])([CH3:33])[CH3:32]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 135706155HCID 135706155, compound

Product 1

HCID 135710948HCID 135710948, compoundYield 84.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of N,N′-bis(tert-butoxycarbonyl)-N″-(3-(3-methoxycarbonylpyridin-2-yl)phenyl)guanidine (282 mg) in methanol (3 ml) was added an aqueous sodium hydroxide solution (1N, 1.2 ml), and the mixture was stirred for 2 hours. The pH of the reaction mixture was adjusted to 5 with 1N hydrochloric acid. The mixture was diluted with water and extracted with ethyl acetate. The separated organic layer was washed with brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was triturated with diisopropyl ether, filtered and dried to give N,N′-bis(tert-butoxycarbonyl)-N″-(3-(3-carboxypyridin-2-yl)phenyl)guanidine (0.23 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe separated organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was triturated with diisopropyl ether
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-5529e192db424b379c50158031735193
Source dataset
uspto-grants-2003_02
Patent number
US06521643B1

Reaction notes

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