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

HRID 1454987Notes

Reaction equation

HRID 1454987 reaction equation
[OH:1][CH2:2][C:3]([NH:5][CH3:6])=[O:4].C(N(C(C)C)CC)(C)C.Cl[C:17]([O:19][C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=1)=[O:18]>ClCCl>[C:17](=[O:18])([O:1][CH2:2][C:3]([NH:5][CH3:6])=[O:4])[O:19][C:20]1[CH:21]=[CH:22][C:23]([N+:26]([O-:28])=[O:27])=[CH:24][CH:25]=1

Participants

5

Reactant 3

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

Product 1

HCID 602095484-Nitrophenyl 2-(methylamino)-2-oxoethyl carbonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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, loading=3.56 mmol/g) in 250 ml of dichloromethane is admixed in small portions and at ambient temperature with 5.93 g (29.4 mmol) of 4-nitrophenyl chloroformate. Orbital stirring is continued at ambient temperature for 16 hours. The resin is filtered off and rinsed with 150 ml of dichloromethane and the filtrate is concentrated under reduced pressure. This gives 6 g of product in the form or a light yellow solid, which is used as it is 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-740ba2a279864af7b5c5aa36f9a21bb0
Source dataset
uspto-grants-2009_01
Patent number
US07482346B2

Reaction notes

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