Trifluoroacetic acid → 1-(cyanomethyl) 4-(2-(ethyldisulfanyl)-6-methylphenyl) (S)-2-((tert-butoxycarbonyl)amino)succinate

HRID 1482267Notes

Reaction equation

HRID 1482267 reaction equation
FC(F)(F)C(O)=O.[C:8]([O:12][C:13]([NH:15][C@@H:16]([CH2:29][C:30]([O:32][C:33]1[C:38]([CH3:39])=[CH:37][CH:36]=[CH:35][C:34]=1[S:40][S:41][CH2:42][CH3:43])=[O:31])[C:17]([O:19][C:20](C1C=CC=CC=1)(C)[CH3:21])=[O:18])=[O:14])([CH3:11])([CH3:10])[CH3:9].CC[N:46](C(C)C)C(C)C>ClCCl.BrCC#N>[C:8]([O:12][C:13]([NH:15][C@@H:16]([CH2:29][C:30]([O:32][C:33]1[C:38]([CH3:39])=[CH:37][CH:36]=[CH:35][C:34]=1[S:40][S:41][CH2:42][CH3:43])=[O:31])[C:17]([O:19][CH2:20][C:21]#[N:46])=[O:18])=[O:14])([CH3:11])([CH3:10])[CH3:9]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acid2×HCID 81531DiisopropylethylamineHCID 1177360924-(2-(ethyldisulfanyl)-6-methylphenyl) 1-(2-phenylpropan-2-yl) (S)-2-((tert-butoxycarbonyl)amino)succinate2×

Product 1

HCID 896685271-(cyanomethyl) 4-(2-(ethyldisulfanyl)-6-methylphenyl) (S)-2-((tert-butoxycarbonyl)amino)succinateYield 74%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 11534BromoacetonitrileSolvent

Procedure

Trifluoroacetic acid (0.040 ml, 0.519 mmol) was added to a solution of 4-(2-(ethyldisulfanyl)-6-methylphenyl) 1-(2-phenylpropan-2-yl) (S)-2-((tert-butoxycarbonyl)amino)succinate (Compound 110) (240 mg, 0.450 mmol) in dichloromethane (4 ml), and the mixture was stirred at room temperature for 1.5 hours. Trifluoroacetic acid (0.040 ml, 0.519 mmol) was further added and the mixture was stirred at room temperature for 1.5 hours. The reaction solution was then concentrated under reduced pressure. DIPEA (0.259 ml, 1.49 mmol) was added to a solution of the resulting residue in bromoacetonitrile (4.70 ml), and the mixture was stirred at room temperature for 10 minutes. The reaction solution was purified by silica gel column chromatography (hexane/ethyl acetate=100/0→50/50) to afford 1-(cyanomethyl) 4-(2-(ethyldisulfanyl)-6-methylphenyl) (S)-2-((tert-butoxycarbonyl)amino)succinate (Compound 112) (151 mg, 74%).

Workup

  1. stirringthe mixture was stirred at room temperature for 1.5 hours
  2. concentrationThe reaction solution was then concentrated under reduced pressure
  3. stirringthe mixture was stirred at room temperature for 10 minutes
  4. customThe reaction solution was purified by silica gel column chromatography (hexane/ethyl acetate=100/0→50/50)

Sources & evidence

ORD record
ord-f9d4d915010e4f749b77a09b0aec93ed
Source dataset
uspto-grants-2016_08
Patent number
US09409952B2

Reaction notes

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