Bromoacetonitrile → HCID 89668508, compound

HRID 1482328Notes

Reaction equation

HRID 1482328 reaction equation
[CH:1]([N:4](CC)C(C)C)(C)[CH3:2].BrCC#N.[N:14]([C:17]1[CH:54]=[CH:53][C:20]([CH2:21][O:22][C:23]([NH:25][C@@H:26]([CH2:46][S:47][S:48][C:49]([CH3:52])([CH3:51])[CH3:50])[C:27]([NH:29][CH2:30][CH2:31][CH2:32][CH2:33][C@H:34]([NH:38][C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[C:35]([OH:37])=[O:36])=[O:28])=[O:24])=[CH:19][CH:18]=1)=[N+:15]=[N-:16]>C(#N)C>[N:14]([C:17]1[CH:18]=[CH:19][C:20]([CH2:21][O:22][C:23]([NH:25][C@@H:26]([CH2:46][S:47][S:48][C:49]([CH3:52])([CH3:51])[CH3:50])[C:27]([NH:29][CH2:30][CH2:31][CH2:32][CH2:33][C@H:34]([NH:38][C:39]([O:41][C:42]([CH3:45])([CH3:43])[CH3:44])=[O:40])[C:35]([O:37][CH2:2][C:1]#[N:4])=[O:36])=[O:28])=[O:24])=[CH:53][CH:54]=1)=[N+:15]=[N-:16]

Participants

5

Reactant 3

HCID 11534BromoacetonitrileHCID 81531DiisopropylethylamineHCID 89668507HCID 89668507, compound

Product 1

HCID 89668508HCID 89668508, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N,N-Diisopropylethylamine (34 μL, 0.197 mmol) and subsequently bromoacetonitrile (38 μL, 0.539 mmol) were added to a solution of (S)-6-((R)-2-((((4-azidobenzyl)oxy)carbonyl)amino)-3-(tert-butyldisulfanyl)propanamido)-2-((tert-butoxycarbonyl)amino)hexanoic acid (Compound tk23) (110 mg, 0.180 mmol) in acetonitrile (0.3 mL) at room temperature under a nitrogen atmosphere. The reaction mixture was stirred at the same temperature for 15.5 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-((R)-2-((((4-azidobenzyl)oxy)carbonyl)amino)-3-(tert-butyldisulfanyl)propanamido)-2-((tert-butoxycarbonyl)amino)hexanoate (97.3 mg, 83%).

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-baee6e06014b4ff99a224830fd9a0f19
Source dataset
uspto-grants-2016_08
Patent number
US09409952B2

Reaction notes

Loading…