Hydrochloric Acid → HCID 57717477, compound

HRID 2360558Notes

Reaction equation

HRID 2360558 reaction equation
[O:1]=[C:2]1[C:6]2([CH2:11][CH2:10][N:9]([C:12]3[S:13][C:14]([C:17]([O:19]CC)=[O:18])=[CH:15][N:16]=3)[CH2:8][CH2:7]2)[N:5]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:4][NH:3]1.[OH-].[Li+].Cl>O1CCOCC1>[O:1]=[C:2]1[C:6]2([CH2:11][CH2:10][N:9]([C:12]3[S:13][C:14]([C:17]([OH:19])=[O:18])=[CH:15][N:16]=3)[CH2:8][CH2:7]2)[N:5]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:4][NH:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67104532HCID 67104532, compound

Product 1

HCID 57717477HCID 57717477, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Ethyl 2-(4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]dec-8-yl)-1,3-thiazole-5-carboxylate (0.75 g, 1.9 mmol) was made 0.25 M in 1,4-dioxane and to this stirring solution was added 3 equivalents 3M Lithium hydroxide (1.9 mL, 5.8 mmol). The resulting mixture was microwaved at 75° C. for 1 hour. The reaction mixture was then neutralized to pH=6 with 1N aqueous HCl and a white precipitate came out of solution. The precipitate was filtered off and dried in vacuo to give 2-(4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]dec-8-yl)-1,3-thiazole-5-carboxylic acid. The material was carried on without further purification: MS (ESI+): cal'd [M+H]+ 359.1, obs'd 359.1.

Workup

  1. customThe resulting mixture was microwaved at 75° C. for 1 hour
  2. filtrationThe precipitate was filtered off
  3. customdried in vacuo

Sources & evidence

ORD record
ord-0519c627f4904c6e8dc641db3d3a0b5b
Source dataset
uspto-grants-2014_04
Patent number
US08686020B2

Reaction notes

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