Sodium Azide → HCID 117735755, compound

HRID 1482303Notes

Reaction equation

HRID 1482303 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[C:5]([O:9][C:10](=[O:27])[C@@H:11]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:12][CH:13]([S:16][S:17][CH3:18])[CH2:14]Br)([CH3:8])([CH3:7])[CH3:6]>CN(C)C=O>[C:5]([O:9][C:10](=[O:27])[C@@H:11]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:12][CH:13]([S:16][S:17][CH3:18])[CH2:14][N:1]=[N+:2]=[N-:3])([CH3:8])([CH3:6])[CH3:7]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 89668643HCID 89668643, compound2×

Product 1

HCID 117735755HCID 117735755, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium azide (2.44 g, 37.6 mmol) was added to a solution of the crude (S)-5-bromo-2-tert-butoxycarbonylamino-4-methyldisulfanyl-pentanoic acid tert-butyl ester (Compound 32) obtained in the foregoing in N,N-dimethylformamide (100 ml), and the reaction mixture was stirred at room temperature for 6 hours. After completion of the reaction, the insoluble matter was separated by filtration, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by normal-phase silica gel column chromatography (hexane/ethyl acetate) to afford (S)-5-azido-2-tert-butoxycarbonylamino-4-methyldisulfanyl-pentanoic acid tert-butyl ester (Compound 33) (1.87 g, 64%).

Workup

  1. customAfter completion of the reaction
  2. customthe insoluble matter was separated by filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe resulting residue was purified by normal-phase silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-d5b39cc97e804f08b5ba2c8c1713ea3c
Source dataset
uspto-grants-2016_08
Patent number
US09409952B2

Reaction notes

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