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

HRID 2246196Notes

Reaction equation

HRID 2246196 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-3c436b42807f4ba69991b740fbbc7de1
Source dataset
uspto-grants-2010_03
Patent number
US07687503B2

Reaction notes

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