Triethylamine → benzyl 2(S)-[N-(2-morpholinocarbonylethyl)-N-methylaminocarbonyloxy]-3-phenylpropionate

HRID 1649910Notes

Reaction equation

HRID 1649910 reaction equation
[OH:1][C@@H:2]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4].Cl[C:21](OC(Cl)(Cl)Cl)=[O:22].FC(F)(F)C(O)=O.[CH3:35][NH:36][CH2:37][CH2:38][C:39]([N:41]1[CH2:46][CH2:45][O:44][CH2:43][CH2:42]1)=[O:40].C(N(CC)CC)C>O1CCCC1>[O:44]1[CH2:43][CH2:42][N:41]([C:39]([CH2:38][CH2:37][N:36]([C:21]([O:1][C@@H:2]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:3]([O:5][CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[O:4])=[O:22])[CH3:35])=[O:40])[CH2:46][CH2:45]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10426DiphosgeneHCID 10377698Benzyl (S)-(-)-2-hydroxy-3-phenylpropionateHCID 677650164-(N-methyl-beta-alanyl)morpholine trifluoroacetic acid salt

Product 1

HCID 18638991benzyl 2(S)-[N-(2-morpholinocarbonylethyl)-N-methylaminocarbonyloxy]-3-phenylpropionate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of benzyl 2(S)-hydroxy-3-phenylpropionate (513 mg) in dry tetrahydrofuran (10 ml) was added trichloromethyl chloroformate (0.244 ml). The mixture was refluxed for 18 hours. The mixture was cooled to 0° C., and a solution of 4-(N-methyl-β-alanyl)morpholine trifluoroacetic acid salt (1.44 g) and triethylamine (701 mg) in dry tetrahydrofuran (10 ml) was added thereto. The mixture was stirred at ambient temperature for 2 hours. After evaporation of the solvent, the residue was dissolved in ethyl acetate (50 ml). The solution was washed with 50% hydrochloric acid, 1M sodium bicarbonate solution and water successively, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified with silica-gel column chromatography (50% ethyl acetate in n-hexane as eluent) to give benzyl 2(S)-[N-(2-morpholinocarbonylethyl)-N-methylaminocarbonyloxy]-3-phenylpropionate (726 mg) as an oil.

Workup

  1. temperatureThe mixture was refluxed for 18 hours
  2. customAfter evaporation of the solvent
  3. dissolutionthe residue was dissolved in ethyl acetate (50 ml)
  4. washThe solution was washed with 50% hydrochloric acid, 1M sodium bicarbonate solution and water successively
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified with silica-gel column chromatography (50% ethyl acetate in n-hexane as eluent)

Sources & evidence

ORD record
ord-71d2e9d9ef324eaca50ad148d2248d7f
Source dataset
uspto-grants-1990_05
Patent number
US04921855

Reaction notes

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