Ethyl bromoacetate → Ethyl 2-((tert-butoxycarbonyl)(2-(tert-butyldisulfanyl)ethyl)amino)acetate

HRID 1482217Notes

Reaction equation

HRID 1482217 reaction equation
[C:1]([S:5][S:6][CH2:7][CH2:8][NH2:9])([CH3:4])([CH3:3])[CH3:2].Br[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].CCN(C(C)C)C(C)C.[C:26](OC([O-])=O)([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27]>C(Cl)Cl>[C:29]([O:28][C:26]([N:9]([CH2:8][CH2:7][S:6][S:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:27])([CH3:32])([CH3:31])[CH3:30]

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetateHCID 81531DiisopropylethylamineHCID 4340772-(tert-Butyldithio)ethanamine2×HCID 22064466Tert-butyldicarbonate

Product 1

HCID 89668445Ethyl 2-((tert-butoxycarbonyl)(2-(tert-butyldisulfanyl)ethyl)amino)acetateYield 75.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(tert-Butyldisulfanyl)ethanamine (Compound 6c-A, 0.21 g, 1.26 mmol) and ethyl 2-bromoacetate (0.23 g, 1.39 mmol) were dissolved in DCM (6.0 ml), DIPEA (1.10 ml, 6.31 mmol) was added, and the mixture was stirred at room temperature for 17 hours. tert-Butyl dicarbonate (358 mg, 1.64 mmol) was added to the reaction solution, and the mixture was stirred at room temperature for 15 minutes. The reaction solution was then directly purified by column chromatography (hexane:ethyl acetate=4:1) to afford the title compound (334.8 mg, 75%).

Workup

  1. stirringthe mixture was stirred at room temperature for 15 minutes
  2. customThe reaction solution was then directly purified by column chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-c676804a5a324fedb2f1064e5120d8d0
Source dataset
uspto-grants-2016_08
Patent number
US09409952B2

Reaction notes

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