Bromoacetonitrile → HCID 89668619, compound

HRID 1482346Notes

Reaction equation

HRID 1482346 reaction equation
[CH:1]([N:4](CC)C(C)C)(C)[CH3:2].BrCC#N.[NH:14]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[C@H:15]([C:27]([OH:29])=[O:28])[CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:21]([C:23]([F:26])([F:25])[F:24])=[O:22]>C(#N)C>[C:33]([O:32][C:30]([NH:14][C@@H:15]([CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:21](=[O:22])[C:23]([F:25])([F:26])[F:24])[C:27]([O:29][CH2:2][C:1]#[N:4])=[O:28])=[O:31])([CH3:36])([CH3:35])[CH3:34]

Participants

5

Reactant 3

HCID 11534BromoacetonitrileHCID 81531DiisopropylethylamineHCID 7009540N~2~-(tert-Butoxycarbonyl)-N~6~-(trifluoroacetyl)-L-lysine

Product 1

HCID 89668619HCID 89668619, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N,N-Diisopropylethylamine (102 μL, 0.585 mmol) and subsequently bromoacetonitrile (185 μL, 2.66 mmol) were added to a solution of Boc-Lys(Tfa)-OH (Compound tk52) (182 mg, 0.532 mmol) in acetonitrile (0.5 mL) at room temperature under a nitrogen atmosphere. The reaction mixture was stirred at the same temperature for 5.25 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 2-((tert-butoxycarbonyl)amino)-6-(2,2,2-trifluoroacetamido)hexanoate (Compound tk53) (200.8 mg, 99%).

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-cc4b6ed839cd46c5b7613ae819c1b240
Source dataset
uspto-grants-2016_08
Patent number
US09409952B2

Reaction notes

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