Diisopropylethylamine → 4-Nitrophenyl 2-(methylamino)-2-oxoethyl carbonate

HRID 1640403Notes

Reaction equation

HRID 1640403 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)=[O:3].[OH:14][CH2:15][C:16]([NH:18][CH3:19])=[O:17].C(N(C(C)C)CC)(C)C>ClCCl>[C:2](=[O:3])([O:4][C:5]1[CH:6]=[CH:7][C:8]([N+:11]([O-:13])=[O:12])=[CH:9][CH:10]=1)[O:14][CH2:15][C:16]([NH:18][CH3:19])=[O:17]

Participants

5

Reactant 3

HCID 81531Diisopropylethylamine2×HCID 821294-Nitrophenyl chloroformateHCID 2235792-Hydroxy-N-methylacetamide

Product 1

HCID 602095484-Nitrophenyl 2-(methylamino)-2-oxoethyl carbonateYield 80.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5.93 g (29.4 mmol) of 4-nitrophenyl chloroformate are added portionwise and at room temperature to a suspension of 2.62 g (29.4 mmol) of 2-hydroxy-N-methylacetamide and 16.5 g (58.7 mmol) of supported diisopropylethylamine (Ps-DIEA from Argonaut, charge=3.56 mmol/g) in 250 ml of dichloromethane. Orbital stirring is continued at room temperature for 16 hours. The resin is filtered off and rinsed with 150 ml of dichloromethane, and the filtrate is concentrated under reduced pressure. 6 g of product are obtained in the form of a pale yellow solid (purity estimated at 70%), and are used without further purification in the following step.

Workup

  1. filtrationThe resin is filtered off
  2. washrinsed with 150 ml of dichloromethane
  3. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-4bfe5fa758ed4704ab63faf11ca5a3ed
Source dataset
uspto-grants-2012_02
Patent number
US08114866B2

Reaction notes

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