Hydrochloric Acid → HCID 67280836, compound

HRID 1693305Notes

Reaction equation

HRID 1693305 reaction equation
[C:1]([O:5][C:6]([N:8]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[C:9]1[C:10]2[C:11]3[C:12](=[N:24][N:25]([CH2:27][C:28]4[C:33]([CH3:34])=[C:32]([O:35][CH3:36])[C:31]([CH3:37])=[CH:30][N:29]=4)[N:26]=2)[CH:13]=[C:14]([CH2:19][C:20]([O:22]C)=[O:21])[C:15]=3[CH2:16][S:17][N:18]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CO.[OH-].[Na+].Cl>O>[C:1]([O:5][C:6]([N:8]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[C:9]1[C:10]2[C:11]3[C:12](=[N:24][N:25]([CH2:27][C:28]4[C:33]([CH3:34])=[C:32]([O:35][CH3:36])[C:31]([CH3:37])=[CH:30][N:29]=4)[N:26]=2)[CH:13]=[C:14]([CH2:19][C:20]([OH:22])=[O:21])[C:15]=3[CH2:16][S:17][N:18]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium Hydroxide3×HCID 86641343HCID 86641343, compound

Product 1

HCID 67280836HCID 67280836, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture composed of the above methyl {4-[bis(tert-butoxycarbonyl)amino]-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-2,7-dihydro-6-thia-1,2,3,5-tetraazabenzo[cd]azulen-8-yl}acetate (69 mg), methanol (2 ml) and a 1 N sodium hydroxide solution (0.22 ml) was stirred at room temperature for 16 hours. A 1 N sodium hydroxide solution (0.5 ml) was added, followed by stirring for three hours. Then, a 1 N sodium hydroxide solution (0.3 ml) was further added, followed by stirring for three hours. A 1 N hydrochloric acid solution (1.5 ml) was added dropwise to the reaction mixture. Then, water was added, followed by extraction with ethyl acetate. The organic layer was dried over sodium sulfate and filtered. Then, the filtrate was concentrated under reduced pressure. An oil (60 mg, 89%) was obtained as a residue. Although the product contained a by-product, it was directly used for the next reaction without further purification.

Workup

  1. stirringby stirring for three hours
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationThen, the filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1faece0e25e84e0e9278984c04fb8448
Source dataset
uspto-grants-2012_04
Patent number
US08158638B2

Reaction notes

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