Benzyl bromoacetate → HCID 18761090, compound

HRID 2226043Notes

Reaction equation

HRID 2226043 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][NH2:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[CH2:13][C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15].CCN(C(C)C)C(C)C>C(#N)C>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][NH:11][CH2:13][C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 62576Benzyl bromoacetateHCID 81531DiisopropylethylamineHCID 187201N-BOC-ethylenediamine

Product 1

HCID 18761090HCID 18761090, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1.4 g (8.74 mmole) of N-(t-butoxycarbonyl)ethylenediamine (prepared in Example 2, Step A above), 1.35 mL (8.74 mmole) of benzyl 2-bromoacetate, and 1.53 mL (8.74 mmole) of DIEA in 18 mL of acetonitrile was stirred for 18 hr at room temperature. The mixture was then concentrated in vacuo and the residue purified by flash chromatography on 130 g of silica eluting with 2 L of 75:25 hexanes: ethyl acetate then 1 L of 100:4 methylene chloride:methanol to give 1.8 g (67%) of an oil.

Workup

  1. concentrationThe mixture was then concentrated in vacuo
  2. customthe residue purified by flash chromatography on 130 g of silica eluting with 2 L of 75:25 hexanes

Sources & evidence

ORD record
ord-2c4cc38f88d543e3b40e948273586ca2
Source dataset
uspto-grants-1994_09
Patent number
US05344830

Reaction notes

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