Triethylamine → HCID 21993789, compound

HRID 1978376Notes

Reaction equation

HRID 1978376 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.ON1C2C=CC=CC=2N=N1.Cl.Cl.[NH2:26][CH:27]1[CH2:32][CH2:31][N:30]([CH2:33][CH2:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH2:29][CH2:28]1.C1CCN2C(=NCCC2)CC1.C(N(CC)CC)C>C(#N)C>[C:36]1([CH2:35][CH2:34][CH2:33][N:30]2[CH2:31][CH2:32][CH:27]([NH:26][C:10](=[O:12])[CH2:9][NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:28][CH2:29]2)[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 78288N-(tert-butoxycarbonyl)glycineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 27960291-Hydroxybenzotriazole hydrateHCID 219940191-(3-Phenylpropyl)piperidin-4-amine--hydrogen chloride (1/2)

Product 1

HCID 21993789HCID 21993789, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a suspension of 4.21 g (24.03 mmol.) of N-tert-butoxycarbonyl glycine and 5.51 g (35.98 mmol.) of 1-hydroxybenzotriazole monohydrate in acetonitrile (30 ml) was added, at room temperature, 6.90 g (36.0 mmol.) of N-ethyl-N′-3-(N,N-dimethylamino)propylcarboxiimide hydrochloride. The mixture was stirred for one hour. To the reaction system was then added a solution of 7.00 g (24.03 mmol.) of 4-amino-1-(3-phenylpropan-1-yl)piperidine dihydrochloride, 7.32 g (48.08 mmol.) of 1,8-bicyclo[5.4.0]unde-7-cene (DBU) and 3.4 ml (24.4 mmol.) of triethylamine in acetonitrile (20 ml). The mixture was stirred for 2 hours at room temperature. The solvent was distilled off under reduced pressure. To the residue was added chloroform. The mixture was washed with water and a saturated aqueous saline solution, followed by drying over magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by means of a column chromatography (methanol/ethyl acetate 30%). The solvent was distilled off under reduced pressure to give the object compound as a yellowish orange liquid product. The yield was 5.35 g (59%).

Workup

  1. additionwas added, at room temperature
  2. stirringThe mixture was stirred for 2 hours at room temperature
  3. distillationThe solvent was distilled off under reduced pressure
  4. additionTo the residue was added chloroform
  5. washThe mixture was washed with water
  6. dry with materialby drying over magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customThe residue was purified by means of a column chromatography (methanol/ethyl acetate 30%)
  9. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-81dee961f54b4848a0c4e4957ede33e9
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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