Triethylamine → HCID 86723485, compound

HRID 2201248Notes

Reaction equation

HRID 2201248 reaction equation
[C:1]([C:9]1[C:10](=[O:20])[N:11]([CH3:19])[C:12](=[O:18])[N:13]([CH3:17])[C:14]=1[CH2:15]Br)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:21][C@@H:22]([CH2:33][CH2:34][C:35]([O:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:36])[C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24].C(N(CC)CC)C>O1CCOCC1>[CH3:17][N:13]1[C:14]2=[CH:15][N:21]([C@@H:22]([CH2:33][CH2:34][C:35]([O:37][CH2:38][C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)=[O:36])[C:23]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:24])[C:1]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[C:9]2[C:10](=[O:20])[N:11]([CH3:19])[C:12]1=[O:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9503195-Benzoyl-6-(bromomethyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione2×HCID 3037947L-Glutamic acid dibenzyl ester

Product 1

HCID 86723485HCID 86723485, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

5-benzoyl-6-(bromomethyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione (Intermediate C) (2.04 g, 6.05 mmol), (S)-dibenzyl 2-aminopentanedioate (commercially available) (4.53 g, 9.08 mmol) and triethylamine (3.37 mL, 24.20 mmol) were suspended in dioxane (30 mL) and the mixture was heated at reflux for 2 hours. The mixture was cooled to room temperature and evaporated under vacuum. The residue was partitioned between DCM and 0.1M HCl(aq) and the phases separated. The organic phase was passed through a hydrophobic frit. Purification by chromatography on silica, eluting with 20-60% EtOAc/hexane, afforded the title compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 2 hours
  3. customevaporated under vacuum
  4. customThe residue was partitioned between DCM and 0.1M HCl(aq)
  5. customthe phases separated
  6. customPurification by chromatography on silica
  7. washeluting with 20-60% EtOAc/hexane

Sources & evidence

ORD record
ord-4592ce806c7f4fbeb690cd594a4e135c
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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