Piperidine → (R)-3-(tert-butyldisulfanyl)-2-(methylamino)propanoic acid

HRID 1482212Notes

Reaction equation

HRID 1482212 reaction equation
N1CCCCC1.C1C2C(CO[C:22]([N:24](C)[C@@H:25]([CH2:29][S:30][S:31][C:32]([CH3:35])([CH3:34])[CH3:33])[C:26]([OH:28])=[O:27])=O)C3C(=CC=CC=3)C=2C=CC=1>O1CCCC1>[C:32]([S:31][S:30][CH2:29][C@H:25]([NH:24][CH3:22])[C:26]([OH:28])=[O:27])([CH3:35])([CH3:34])[CH3:33]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 75409952Fmoc-N-methyl-S-tert-butylthio-L-cysteine

Product 1

HCID 89668411(R)-3-(tert-butyldisulfanyl)-2-(methylamino)propanoic acidYield 45.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Piperidine (1.8 ml, 18.2 mmol) was added to a solution of (R)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-(tert-butyldisulfanyl)propanoic acid (Compound 2c-B) (2.70 g, 6.06 mmol) in tetrahydrofuran (20 ml), and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was then concentrated under reduced pressure, and the residue was purified by reverse-phase silica gel column chromatography (10 mM aqueous ammonium acetate solution/methanol=100/0→60/40) to afford (R)-3-(tert-butyldisulfanyl)-2-(methylamino)propanoic acid (Compound 2f-G) (610 mg, 45%).

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. customthe residue was purified by reverse-phase silica gel column chromatography (10 mM aqueous ammonium acetate solution/methanol=100/0→60/40)

Sources & evidence

ORD record
ord-188bde7f682d40c5a6d51dc6f665f221
Source dataset
uspto-grants-2016_08
Patent number
US09409952B2

Reaction notes

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