HCID 18474608, compound → HCID 53639334, compound

HRID 2187618Notes

Reaction equation

HRID 2187618 reaction equation
C(OC([NH:8][CH:9]([CH2:20][CH2:21][S:22][CH3:23])[C:10]([O:12][CH:13]1[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]1)=[O:11])=O)(C)(C)C>ClCCl.C(O)(C(F)(F)F)=O>[CH3:19][N:16]1[CH2:15][CH2:14][CH:13]([O:12][C:10](=[O:11])[C@H:9]([CH2:20][CH2:21][S:22][CH3:23])[NH2:8])[CH2:18][CH2:17]1

Participants

4

Reactant 1

HCID 18474608HCID 18474608, compound

Product 1

HCID 53639334HCID 53639334, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of the 1-methylpiperidin-4-yl 2-tert-butoxycarbonylamino-4-methylsulfanylbutyrate (3.8 g; 11 mmol) in dichloromethane (5 ml) and TFA (10 ml) was stirred at ambient temperature for 2 hours. After evaporation to dryness, the residue was redissolved in dichloromethane and treated with a solution of 3.8 M HCl in ether (6 ml) at 0° C. The resulting precipitate was triturated with ether and filtrated to give L-methionine (N-methylpiperidin-4-yl) ester.

Workup

  1. customAfter evaporation to dryness
  2. dissolutionthe residue was redissolved in dichloromethane
  3. additiontreated with a solution of 3.8 M HCl in ether (6 ml) at 0° C
  4. customThe resulting precipitate was triturated with ether
  5. filtrationfiltrated

Sources & evidence

ORD record
ord-863fcce9af8f46efa212d0173b772986
Source dataset
uspto-grants-2002_06
Patent number
US06410539B1

Reaction notes

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