Triethylamine → HCID 136085209, compound

HRID 1893210Notes

Reaction equation

HRID 1893210 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:29][CH3:30])[CH:9]([C:17]1[NH:18][C:19](=[O:28])[C:20]([OH:27])=[C:21]([C:23]([O:25]C)=O)[N:22]=1)[CH2:10][CH2:11][C@H:12]([O:15][CH3:16])[CH2:13][OH:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:31][C:32]1[CH:39]=[CH:38][C:35]([CH2:36][NH2:37])=[CH:34][CH:33]=1.C(N(CC)CC)C>CO.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[CH2:29]([N:8]([CH:9]([C:17]1[NH:18][C:19](=[O:28])[C:20]([OH:27])=[C:21]([C:23]([NH:37][CH2:36][C:35]2[CH:38]=[CH:39][C:32]([F:31])=[CH:33][CH:34]=2)=[O:25])[N:22]=1)[CH2:10][CH2:11][C@H:12]([O:15][CH3:16])[CH2:13][OH:14])[C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[CH3:30]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 673264-FluorobenzylamineHCID 136085211HCID 136085211, compound

Product 1

HCID 136085209HCID 136085209, compound

Reagents, catalysts & solvents 2

HCID 311Citric AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of methyl 2-{(4S)-1-[(tert-butoxycarbonyl)(ethyl)amino]-5-hydroxy-4-methoxypentyl}-5-hydroxy-6-oxo-1,6-dihydropyrimidine-4-carboxylate (48 g, 112 mmol) in MeOH (1118 mL) was added 4-fluoro-benzylamine (28 g, 224 mmol) and triethylamine (31.2 mL, 224 mmol). The resulting mixture was sealed and heated at 80° C. overnight. The reaction mixture was cooled to ambient temperature, diluted with 10% citric acid (˜100 mL), and extracted with DCM (3×). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. The crude residue was dissolved in acetonitrile and concentrated under reduced pressure (3×) to remove MeOH. The residue was dried under high vacuum for 2 days and used in the next reaction without purification. LC-MS: 523.5 (M+1).

Workup

  1. customThe resulting mixture was sealed
  2. temperatureThe reaction mixture was cooled to ambient temperature
  3. extractionextracted with DCM (3×)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. dissolutionThe crude residue was dissolved in acetonitrile
  8. concentrationconcentrated under reduced pressure (3×)
  9. customto remove MeOH
  10. customThe residue was dried under high vacuum for 2 days
  11. customused in the next reaction without purification

Sources & evidence

ORD record
ord-821f1e7af5404ca29be4c73623e0a8c0
Source dataset
uspto-grants-2013_08
Patent number
US08513234B2

Reaction notes

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