Bromoacetonitrile → Cyanomethyl 2-((tert-butoxycarbonyl) (2-(tert-butyldisulfanyl)ethyl)amino)acetate

HRID 1482219Notes

Reaction equation

HRID 1482219 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:13][CH2:14][S:15][S:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:9][C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[CH2:22][C:23]#[N:24].CCN(C(C)C)C(C)C.[Cl-].[NH4+]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]([CH2:13][CH2:14][S:15][S:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:9][C:10]([O:12][CH2:22][C:23]#[N:24])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 11534BromoacetonitrileHCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 896683122-((Tert-butoxycarbonyl)(2-(tert-butyldisulfanyl)ethyl)amino)acetic acid2×

Product 1

HCID 89668269Cyanomethyl 2-((tert-butoxycarbonyl) (2-(tert-butyldisulfanyl)ethyl)amino)acetateYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-((tert-Butoxycarbonyl)(2-(tert-butyldisulfanyl)ethyl)amino)acetic acid (Compound 6f-A, 268.1 mg, 0.83 mmol) and 2-bromoacetonitrile (199 mg, 1.66 mmol) were dissolved in DMF (1.0 ml), DIPEA (0.43 ml, 2.49 mmol) was added and the mixture was stirred at room temperature for 15 minutes. A saturated aqueous ammonium chloride solution was added to the reaction solution, followed by extraction with diethyl ether. The resulting organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by column chromatography (hexane:ethyl acetate=3:1) to afford the title compound (287.7 mg, 96%).

Workup

  1. extractionfollowed by extraction with diethyl ether
  2. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by column chromatography (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-e727c817362c4425a625df14cb9cca0e
Source dataset
uspto-grants-2016_08
Patent number
US09409952B2

Reaction notes

Loading…