Triethylamine → methyl 2(S)-[N-methyl-N-[2-{N-(morpholinocarbonyl)-N-methylamino}ethyl]aminocarbonyloxy]-3-phenylpropionate

HRID 259835Notes

Reaction equation

HRID 259835 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][N:5]([C:7]([O:9][C@@H:10]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:11]([O:13][CH3:14])=[O:12])=[O:8])[CH3:6].C(N(CC)CC)C.[O:29]1[CH2:34][CH2:33][N:32]([C:35](Cl)=[O:36])[CH2:31][CH2:30]1>C(Cl)Cl>[CH3:6][N:5]([C:7]([O:9][C@@H:10]([CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:11]([O:13][CH3:14])=[O:12])=[O:8])[CH2:4][CH2:3][N:2]([C:35]([N:32]1[CH2:33][CH2:34][O:29][CH2:30][CH2:31]1)=[O:36])[CH3:1]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 848104-Morpholinecarbonyl chlorideHCID 22861688Methyl 2(S)-[N-(2-methylaminoethyl)-N-methylaminocarbonyloxy]-3-phenylpropionate

Product 1

HCID 22861689methyl 2(S)-[N-methyl-N-[2-{N-(morpholinocarbonyl)-N-methylamino}ethyl]aminocarbonyloxy]-3-phenylpropionateYield 88.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 2(S)-[N-(2-methylaminoethyl)-N-methylaminocarbonyloxy]- 3-phenylpropionate (8.0 g) was dissolved in methylene chloride (40 ml), and triethylamine (4.13 g) was added thereto under cooling. Thereto was dropwise added morpholinocarbonyl chloride (4.07 g) at 0°-10° C. over 30 minutes. After the dropwise addition, the mixture was stirred at said temperature for 60 minutes, washed with 5% hydrochloric acid, water, an aqueous solution of 6% sodium hydrogencarbonate, and water in this order, and the solvent was evaporated under reduced pressure to give 9.83 g of methyl 2(S)-[N-methyl-N-[2-{N-(morpholinocarbonyl)-N-methylamino}ethyl]aminocarbonyloxy]-3-phenylpropionate (yield 88.8%).

Workup

  1. temperatureunder cooling
  2. customat 0°-10° C.
  3. customover 30 minutes
  4. additionAfter the dropwise addition
  5. customfor 60 minutes
  6. washwashed with 5% hydrochloric acid, water
  7. customan aqueous solution of 6% sodium hydrogencarbonate, and water in this order, and the solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-baf78fb8b36846b9953f1c0997b74ec9
Source dataset
uspto-grants-1996_06
Patent number
US05523410

Reaction notes

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