Chlorotrimethylsilane → HCID 117736116, compound

HRID 1482307Notes

Reaction equation

HRID 1482307 reaction equation
[Cl:1][Si](C)(C)C.C([O:10][C:11](=[O:33])[C@@H:12]([NH:25]C(OC(C)(C)C)=O)[CH2:13][CH:14]([S:19][S:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:15][N:16]=[N+:17]=[N-:18])(C)(C)C>FC(F)(F)CO>[ClH:1].[NH2:25][C@@H:12]([CH2:13][CH:14]([S:19][S:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:15][N:16]=[N+:17]=[N-:18])[C:11]([OH:33])=[O:10]

Participants

4

Reactant 2

HCID 6397Chlorotrimethylsilane2×HCID 117736433HCID 117736433, compound2×

Product 1

HCID 117736116HCID 117736116, compoundYield 97.5%

Reagents, catalysts & solvents 1

HCID 64092,2,2-TrifluoroethanolSolvent

Procedure

Chlorotrimethylsilane (467 μl, 2.344 mmol) was added to a solution of (S)-5-azido-2-tert-butoxycarbonylamino-4-tert-butyldisulfanyl-pentanoic acid tert-butyl ester (Compound 39) (160 mg, 0.368 mmol) in 2,2,2-trifluoroethanol (3.2 ml), and the mixture was stirred at room temperature for 2 hours. Chlorotrimethylsilane (467 μl, 2.344 mmol) was further added, and the reaction solution was stirred at room temperature for 3 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-tert-butyldisulfanyl-pentanoic acid hydrochloride (Compound 40) (113 mg, 97%).

Workup

  1. stirringthe reaction solution was stirred at room temperature for 3 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-0198516ee9e64fb9a52ce5338757b7c8
Source dataset
uspto-grants-2016_08
Patent number
US09409952B2

Reaction notes

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