Triethylamine → HCID 58116511, compound

HRID 661256Notes

Reaction equation

HRID 661256 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[CH:12]1[CH2:17][NH:16][CH2:15][CH:14]([C:18]([O:20][CH3:21])=[O:19])[CH2:13]1.C(N(CC)CC)C.Cl[C:30]([O:32][C:33]1[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=1)=[O:31]>ClCCl>[F:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:9])[F:10])[CH:5]=[CH:4][C:3]=1[CH:12]1[CH2:17][N:16]([C:30]([O:32][C:33]2[CH:34]=[CH:35][C:36]([N+:39]([O-:41])=[O:40])=[CH:37][CH:38]=2)=[O:31])[CH2:15][CH:14]([C:18]([O:20][CH3:21])=[O:19])[CH2:13]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformateHCID 58116527HCID 58116527, compound

Product 1

HCID 58116511HCID 58116511, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

938 mg (3.07 mmol) of the compound from Example 87A were initially charged in 40 ml of dichloromethane and cooled to 0° C., and admixed with 1.28 ml (0.93 g, 9.22 mmol) of triethylamine and 0.62 g (3.07 mmol) of 4-nitrophenyl chloroformate. The reaction mixture was allowed to warm up slowly to RT and stirred at RT for 16 h. It was washed repeatedly with water, dried over sodium sulphate, filtered and concentrated under reduced pressure. This gave 1.21 g of crude product in 85% purity (LC-MS), which was reacted without any further purification steps.

Workup

  1. temperatureto warm up slowly to RT
  2. washIt was washed repeatedly with water
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThis gave 1.21 g of crude product in 85% purity (LC-MS), which was reacted without any further purification steps

Sources & evidence

ORD record
ord-3bba4c3b8cde42bdaea57e51d8184f8a
Source dataset
uspto-grants-2011_12
Patent number
US08084469B2

Reaction notes

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