Hydrochloric Acid → HCID 57883817, compound

HRID 2384205Notes

Reaction equation

HRID 2384205 reaction equation
C([O:5][C:6](=[O:31])[CH2:7][NH:8][CH2:9][C:10]1[S:14][C:13]([NH:15][C:16]([N:18]([CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)[CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)=[O:17])=[N:12][CH:11]=1)(C)(C)C.Cl>C(Cl)Cl.C(OCC)C>[CH:25]1([N:18]([CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[C:16](=[O:17])[NH:15][C:13]2[S:14][C:10]([CH2:9][NH:8][CH2:7][C:6]([OH:31])=[O:5])=[CH:11][N:12]=2)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 57883772HCID 57883772, compound

Product 1

HCID 57883817HCID 57883817, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

{[2-(3,3-Dicyclohexyl-ureido)-thiazol-5-ylmethyl]-amino}-acetic acid tert-butyl ester (14 mg, 0.03 mmol) was dissolved in methylene chloride. Hydrogen chloride (100 μL, 4N in dioxane) was added and the reaction was stirred at ambient temperature until no ester could be detected. The reaction was diluted with diethyl ether and concentrated. The resulting residue was dissolved in a minimum amount of methylene chloride, precipitated with diethyl ether and decanted. This was repeated to afford 9 mg (69%) of the desired compound. HPLC-MS: m/z 395 (M+1).

Workup

  1. concentrationconcentrated
  2. dissolutionThe resulting residue was dissolved in a minimum amount of methylene chloride
  3. customprecipitated with diethyl ether
  4. customdecanted

Sources & evidence

ORD record
ord-a95afcdad1b547b5ab4cd3685099b973
Source dataset
uspto-grants-2012_09
Patent number
US08263634B2

Reaction notes

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