Triethylamine → HCID 117951687, compound

HRID 626350Notes

Reaction equation

HRID 626350 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]([C:18]([NH:20][C:21]3[CH:22]=[C:23](/[CH:27]=[CH:28]/[C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH:24]=[CH:25][CH:26]=3)=[O:19])[C:11]3[C:16]([CH:17]=2)=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:5]=[CH:6][CH:7]=1.C[CH2:35][N:36]([CH2:39]C)[CH2:37]C.ClC(OC1C=CC([N+]([O-])=O)=CC=1)=[O:43].Cl.CNC>C(Cl)Cl>[CH3:35][N:36]([CH3:39])[C:37]([O:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]([C:18]([NH:20][C:21]3[CH:22]=[C:23](/[CH:27]=[CH:28]/[C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH:24]=[CH:25][CH:26]=3)=[O:19])[C:11]3[C:16]([CH:17]=2)=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:5]=[CH:6][CH:7]=1)=[O:43]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 821294-Nitrophenyl chloroformateHCID 117951670HCID 117951670, compound

Product 1

HCID 117951687HCID 117951687, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a flask containing 24a (0.9 mmol, 1.0 equivalent) in 10 mL of anhydrous CH2Cl2 was added NEt3 (4.57 mmol, 5.0 equivalents). 4-nitrophenyl chloroformate (1.37 mmol, 1.5 equivalents) was added slowly to the reaction flask at 0° C., and the solution was stirred until the reaction was complete (3 h) as determined by TLC. N,N-dimethylamine hydrochloride (2.74 mmol, 3 equivalents) was added and the reaction mixture was stirred at room temperature for 2 h. The solution was then diluted with DCM, and washed with water, aqueous K2CO3 solution and brine. The organic layer was dried over Na2SO4, filtered, and the solvent was removed in vacuo. The resulting solid was purified using silica gel column chromatography using EtOAc/Pet Ether as eluent to afford 26 as a white solid.

Workup

  1. custom(3 h)
  2. stirringthe reaction mixture was stirred at room temperature for 2 h
  3. washwashed with water, aqueous K2CO3 solution and brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent was removed in vacuo
  7. customThe resulting solid was purified

Sources & evidence

ORD record
ord-e9f0dde3c687424b9ac6a8f98c34db56
Source dataset
uspto-grants-2016_04
Patent number
US09309187B2

Reaction notes

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