Sodium Chloride → Methyl 2(S)-[N-(2-methylaminoethyl)-N-methylaminocarbonyloxy]-3-phenylpropionate

HRID 259834Notes

Reaction equation

HRID 259834 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][NH:5][CH3:6].[O:7]([C:14]([O:16][C@@H:17]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:18]([O:20][CH3:21])=[O:19])=O)C1C=CC=CC=1.C(OCC)(=O)C.[Cl-].[Na+]>CN(C)C=O>[CH3:1][NH:2][CH2:3][CH2:4][N:5]([C:14]([O:16][C@@H:17]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:18]([O:20][CH3:21])=[O:19])=[O:7])[CH3:6]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 8070N,N'-DimethylethylenediamineHCID 8857Ethyl AcetateHCID 22861691methyl 2(S)-phenoxycarbonyloxy-3-phenylpropionate

Product 1

HCID 22861688Methyl 2(S)-[N-(2-methylaminoethyl)-N-methylaminocarbonyloxy]-3-phenylpropionateYield 97.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To N,N'-dimethylethylenediamine (7.93 g) in N,N-dimethylformamide (27 ml) was dropwise added methyl 2(S)-phenoxycarbonyloxy-3-phenylpropionate (9.0 g) in N,N-dimethylformamide (9 ml) under cooling at -5°-10° C. over 30 minutes. After the dropwise addition, the mixture was stirred at said temperature for 60 minutes and poured into a mixture of ethyl acetate and 20% aqueous sodium chloride for partition. The water layer was re-extracted with ethyl acetate, the organic layer was combined, and 5% hydrochloric acid was added thereto for partition. The water layer was washed with ethyl acetate, added with methylene chloride, and adjusted to pH 9.0 with an aqueous solution of 24% sodium hydroxide. The organic layer was separated, washed with 20% aqueous sodium chloride, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure to give 8.64 g of methyl 2(S)-[N-(2-methylaminoethyl)-N-methylaminocarbonyloxy]-3-phenylpropionate (yield 97.9%).

Workup

  1. temperatureunder cooling at -5°-10° C. over 30 minutes
  2. additionAfter the dropwise addition
  3. customfor 60 minutes
  4. customfor partition
  5. extractionThe water layer was re-extracted with ethyl acetate
  6. addition5% hydrochloric acid was added
  7. customfor partition
  8. washThe water layer was washed with ethyl acetate
  9. additionadded with methylene chloride
  10. customThe organic layer was separated
  11. washwashed with 20% aqueous sodium chloride
  12. dry with materialdried over magnesium sulfate
  13. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-3798887cb3dc4cd3bad211c2a7850885
Source dataset
uspto-grants-1996_06
Patent number
US05523410

Reaction notes

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