Bromoacetonitrile → (S)-cyanomethyl 6-azido-2-((tert-butoxycarbonyl)amino)hexanoate

HRID 1482343Notes

Reaction equation

HRID 1482343 reaction equation
[CH:1]([N:4](CC)C(C)C)(C)[CH3:2].BrCC#N.[N:14]([CH2:17][CH2:18][CH2:19][CH2:20][C@H:21]([NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C:22]([OH:24])=[O:23])=[N+:15]=[N-:16]>C(#N)C>[N:14]([CH2:17][CH2:18][CH2:19][CH2:20][C@H:21]([NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C:22]([O:24][CH2:2][C:1]#[N:4])=[O:23])=[N+:15]=[N-:16]

Participants

5

Reactant 3

HCID 11534BromoacetonitrileHCID 81531DiisopropylethylamineHCID 251460616-Azido-N-(tert-butoxycarbonyl)-L-norleucine

Product 1

HCID 89668729(S)-cyanomethyl 6-azido-2-((tert-butoxycarbonyl)amino)hexanoateYield 109.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N,N-Diisopropylethylamine (99 μL, 0.566 mmol) and subsequently bromoacetonitrile (179 μL, 2.57 mmol) were added to a solution of (S)-6-azido-2-((tert-butoxycarbonyl)amino)hexanoic acid (Compound tk48) (140 mg, 0.514 mmol) in acetonitrile (0.6 mL) at room temperature under a nitrogen atmosphere. The reaction mixture was stirred at the same temperature for 3.75 hours and then concentrated under reduced pressure, and the resulting crude product was purified by normal-phase silica gel column chromatography (hexane/ethyl acetate) to afford (S)-cyanomethyl 6-azido-2-((tert-butoxycarbonyl)amino)hexanoate (Compound tk49) (175 mg, quant.).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customthe resulting crude product was purified by normal-phase silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-0cffa2f0e5354358ad6f606e24778ce6
Source dataset
uspto-grants-2016_08
Patent number
US09409952B2

Reaction notes

Loading…