Chlorotrimethylsilane → HCID 117736028, compound

HRID 1482304Notes

Reaction equation

HRID 1482304 reaction equation
[Cl:1][Si](C)(C)C.C([O:10][C:11](=[O:30])[C@@H:12]([NH:22]C(OC(C)(C)C)=O)[CH2:13][CH:14]([S:19][S:20][CH3:21])[CH2:15][N:16]=[N+:17]=[N-:18])(C)(C)C>FC(F)(F)CO>[ClH:1].[NH2:22][C@@H:12]([CH2:13][CH:14]([S:19][S:20][CH3:21])[CH2:15][N:16]=[N+:17]=[N-:18])[C:11]([OH:30])=[O:10]

Participants

4

Reactant 2

HCID 6397Chlorotrimethylsilane2×HCID 117735755HCID 117735755, compound2×

Product 1

HCID 117736028HCID 117736028, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 64092,2,2-TrifluoroethanolSolvent

Procedure

Chlorotrimethylsilane (297 μl, 2.344 mmol) was added to a solution of (S)-5-azido-2-tert-butoxycarbonylamino-4-methyldisulfanyl-pentanoic acid tert-butyl ester (Compound 33) (92 mg, 0.234 mmol) in 2,2,2-trifluoroethanol (0.9 ml), and the mixture was stirred at room temperature for 2 hours. Chlorotrimethylsilane (150 μl, 1.184 mmol) was further added, and the reaction solution was stirred at room temperature for 12 hours. After completion of the reaction, the reaction solution was concentrated under reduced pressure, and the resulting residue was washed with a mixed solvent of hexane/ethyl acetate/dichloromethane (3:1:0.1) to afford (S)-2-amino-5-azido-4-methyldisulfanyl-pentanoic acid hydrochloride (Compound 34) (58 mg, 91%).

Workup

  1. stirringthe reaction solution was stirred at room temperature for 12 hours
  2. customAfter completion of the reaction
  3. concentrationthe reaction solution was concentrated under reduced pressure
  4. washthe resulting residue was washed with a mixed solvent of hexane/ethyl acetate/dichloromethane (3:1:0.1)

Sources & evidence

ORD record
ord-276fdf54414e400da1afee533f2f7ffe
Source dataset
uspto-grants-2016_08
Patent number
US09409952B2

Reaction notes

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