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

HRID 1008862Notes

Reaction equation

HRID 1008862 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-25043e9be25341f3815335c0ddfdb773
Source dataset
uspto-grants-2011_07
Patent number
US07973042B2

Reaction notes

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