Diisopropylethylamine → 2-(Methylamino)-2-oxoethyl 1,1'-biphenyl-4-ylmethylcarbamate

HRID 1867532Notes

Reaction equation

HRID 1867532 reaction equation
[CH3:1][NH:2][C:3](=[O:6])[CH2:4][OH:5].Cl[C:8](OC1C=CC([N+]([O-])=O)=CC=1)=[O:9].C(N(CC)C(C)C)(C)C.[C:29]1([C:35]2[CH:42]=[CH:41][C:38]([CH2:39][NH2:40])=[CH:37][CH:36]=2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C(Cl)Cl>[C:35]1([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:36]=[CH:37][C:38]([CH2:39][NH:40][C:8](=[O:9])[O:5][CH2:4][C:3]([NH:2][CH3:1])=[O:6])=[CH:41][CH:42]=1

Participants

6

Reactant 4

HCID 81531Diisopropylethylamine2×HCID 821294-Nitrophenyl chloroformateHCID 2235792-Hydroxy-N-methylacetamideHCID 3449894-Phenylbenzylamine

Product 1

HCID 104024172-(Methylamino)-2-oxoethyl 1,1'-biphenyl-4-ylmethylcarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

0.1 g (0.97 mmol) of N-methyl-2-hydroxyacetamide is admixed dropwise at ambient temperature with a solution of 0.196 g (0.97 mmol) of 4-nitrophenyl chloroformate in 3 ml of methylene chloride and 0.166 ml (0.97 mmol) of N,N-diisopropylethylamine. The mixture is stirred at ambient temperature for 45 minutes and then a solution of 0.195 g (1.067 mmol) of 4-phenylbenzylamine in 3 ml of methylene chloride and 0.166 ml (0.97 mmol) of N,N-diisopropylethylamine is added dropwise at ambient temperature. The mixture is stirred at ambient temperature for 1 hour. It is washed with saturated aqueous ammonium chloride solution, with aqueous 10% sodium carbonate solution and with saturated aqueous sodium chloride solution. The phases are separated and the organic phase is dried over sodium sulphate. The system is filtered, the filtrate is concentrated under reduced pressure and the residue is purified by chromatography on silica gel using ethyl acetate.

Workup

  1. stirringThe mixture is stirred at ambient temperature for 1 hour
  2. washIt is washed with saturated aqueous ammonium chloride solution, with aqueous 10% sodium carbonate solution and with saturated aqueous sodium chloride solution
  3. customThe phases are separated
  4. dry with materialthe organic phase is dried over sodium sulphate
  5. filtrationThe system is filtered
  6. concentrationthe filtrate is concentrated under reduced pressure
  7. customthe residue is purified by chromatography on silica gel

Sources & evidence

ORD record
ord-e81b64a83b3046e0870e14328cde0eb3
Source dataset
uspto-grants-2009_12
Patent number
US07632850B2

Reaction notes

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