Triethylamine → (S)-2-((tert-butoxycarbonyl)amino)-6-(((3-nitropyridin-2-yl)thio)amino)hexanoic acid

HRID 1482367Notes

Reaction equation

HRID 1482367 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C:7]([OH:9])=[O:8].[N+:18]([C:21]1[C:22]([S:27]Cl)=[N:23][CH:24]=[CH:25][CH:26]=1)([O-:20])=[O:19].C(N(CC)CC)C>ClCCl>[C:14]([O:13][C:11]([NH:10][C@@H:6]([CH2:5][CH2:4][CH2:3][CH2:2][NH:1][S:27][C:22]1[C:21]([N+:18]([O-:20])=[O:19])=[CH:26][CH:25]=[CH:24][N:23]=1)[C:7]([OH:9])=[O:8])=[O:12])([CH3:17])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1292833-Nitro-2-pyridinesulfenylHCID 2733284epsilon-tert-Butyloxycarbonyl-lysine

Product 1

HCID 88124485(S)-2-((tert-butoxycarbonyl)amino)-6-(((3-nitropyridin-2-yl)thio)amino)hexanoic acidYield 14.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-6-Amino-2-((tert-butoxycarbonyl)amino)hexanoic acid (Compound tk86) (270 mg, 1.096 mmol) was added to a solution of nitro-2-pyridinesulfenyl chloride (313 mg, 1.644 mmol) in dichloromethane (30 ml), and triethylamine (1.53 ml, 10.96 mmol) was added dropwise to the suspension over 3 minutes. The reaction solution was stirred at room temperature for 3 hours and then concentrated under reduced pressure using an evaporator, and the resulting residue was purified by reverse-phase silica gel column chromatography (0.1% aqueous formic acid solution/0.1% formic acid-acetonitrile solution) to afford (S)-2-((tert-butoxycarbonyl)amino)-6-(((3-nitropyridin-2-yl)thio)amino)hexanoic acid (Compound tk87) (62 mg, 14%).

Workup

  1. additionwas added dropwise to the suspension over 3 minutes
  2. concentrationconcentrated under reduced pressure
  3. customan evaporator
  4. customthe resulting residue was purified by reverse-phase silica gel column chromatography (0.1% aqueous formic acid solution/0.1% formic acid-acetonitrile solution)

Sources & evidence

ORD record
ord-52f5973b66904987aed465bfb6c19f87
Source dataset
uspto-grants-2016_08
Patent number
US09409952B2

Reaction notes

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