Triethylamine → (R)-N-benzyl-3-(tert-butyldisulfanyl)-2-(((3-nitropyridin-2-yl)thio)amino)propanamide

HRID 1482371Notes

Reaction equation

[NH2:1][C@@H:2]([CH2:13][S:14][S:15][C:16]([CH3:19])([CH3:18])[CH3:17])[C:3]([NH:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4].C(N(CC)CC)C.[N+:27]([C:30]1[C:31]([S:36]Cl)=[N:32][CH:33]=[CH:34][CH:35]=1)([O-:29])=[O:28]>ClCCl>[CH2:6]([NH:5][C:3](=[O:4])[C@@H:2]([NH:1][S:36][C:31]1[C:30]([N+:27]([O-:29])=[O:28])=[CH:35][CH:34]=[CH:33][N:32]=1)[CH2:13][S:14][S:15][C:16]([CH3:19])([CH3:18])[CH3:17])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

Conditions

Temperature: 0 °C

Procedure

(R)-2-amino-N-benzyl-3-(tert-butyldisulfanyl)propanamide (Compound tk93) (60 mg, 0.201 mmol) and triethylamine (0.034 ml, 0.241 mmol) were dissolved in dichloromethane (1 ml), and the solution was cooled to 0° C. 3-Nitro-2-pyridinesulfenyl chloride (46.0 mg, 0.241 mmol) was added and the mixture was stirred at 0° C. for 2 hours. The reaction solution was concentrated under reduced pressure, and the resulting residue was purified by normal-phase silica gel column chromatography (hexane/ethyl acetate) to afford (R)—N-benzyl-3-(tert-butyldisulfanyl)-2-(((3-nitropyridin-2-yl)thio)amino)propanamide (Compound tk94) (87 mg, 96%).

Workup

concentrationThe reaction solution was concentrated under reduced pressure
customthe resulting residue was purified by normal-phase silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record: ord-f88a04c5367e4930bec0a537f3b83bdd
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409952B2

Reaction notes

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