Hydrochloric Acid → HCID 178422083, compound

HRID 2360293Notes

Reaction equation

HRID 2360293 reaction equation
[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][C@@H:2]2[NH:8][C:9]1[S:10][C:11]([CH2:16][CH:17]2[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]2)([CH3:15])[C:12](=[O:14])[N:13]=1.Cl>CCOC(C)=O>[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][C@@H:2]2[NH:8][C:9]1[S:10][C:11]([CH3:15])([CH2:16][CH:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)[C:12](=[O:14])[N:13]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178451850tert-butyl 4-[[2-[[(2S)-2-bicyclo[2.2.1]heptanyl]amino]-5-methyl-4-oxo-1,3-thiazol-5-yl]methyl]piperidine-1-carboxylate

Product 1

HCID 178422083HCID 178422083, compoundYield 99.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of tert-butyl 4-((2-((2S)-bicyclo[2.2.1]heptan-2-ylamino)-5-methyl-4-oxo-4,5-dihydrothiazol-5-yl)methyl)piperidine-1-carboxylate (1.42 g, 3.37 mmol, 1.0 eq) in 50 mL of a 4.7 M HCl solution in EtOAc was stirred at room temperature. After 4 h, the reaction mixture was concentrated in vacuo. Aqueous Na2CO3 (2.0 M, 20 mL) was then added, and water was removed in vacuo. The residue was then triturated with 10% MeOH—CH2Cl2 (6×100 mL), and the combined triturating solution were concentrated in vacuo. The crude product was dissolved in CH2Cl2, filtered, and concentrated in vacuo to afford the title compound as a light orange solid (1.08 g). MS (ESI, pos. ion) m/z: 322 (M+H).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. additionAqueous Na2CO3 (2.0 M, 20 mL) was then added
  3. customwater was removed in vacuo
  4. customThe residue was then triturated with 10% MeOH—CH2Cl2 (6×100 mL)
  5. customthe combined triturating solution
  6. concentrationwere concentrated in vacuo
  7. dissolutionThe crude product was dissolved in CH2Cl2
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c26f97a377d44ea6ae955812f6b75af5
Source dataset
uspto-grants-2014_04
Patent number
US08686011B2

Reaction notes

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