Ethylamine → HCID 15660976, compound

HRID 35868Notes

Reaction equation

HRID 35868 reaction equation
[CH2:1]([N:8]([CH3:25])[C:9]([CH2:11][CH2:12][C:13]([N:15]1[CH2:19][CH2:18][CH2:17][C@H:16]1[C:20](=[O:24])[C:21]([OH:23])=O)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:26]([N:28](CC)CC)[CH3:27].ClC(OCC(C)C)=O.C(N)C>C1COCC1.O>[CH2:1]([N:8]([CH3:25])[C:9]([CH2:11][CH2:12][C:13]([N:15]1[CH2:19][CH2:18][CH2:17][C@H:16]1[C:20](=[O:24])[C:21]([NH:28][CH2:26][CH3:27])=[O:23])=[O:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 6341EthylamineHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 15660953[(2S)-1-[3-(N-benzyl-N-methylcarbamoyl)propanoyl]pyrrolidin-2-yl]-2-oxoacetic acid

Product 1

HCID 15660976HCID 15660976, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2 [(2S)-1-[3-(N-benzyl-N-methylcarbamoyl) propanoyl]pyrrolidin-2-yl]-2-oxoacetic acid (98 mg) in THF (3 ml) was cooled to -20° C. Triethylamine (188 μl) and isobutyl chloroformate (77 μl) were added dropwise to the solution. The mixture was stirred for 20 mins at the same temperature. An aq. solution of ethylamine (70% ; 200 μl) was added dropwise to the solution at the same temperature. The solution was stirred for 1 hr, while the temperature of the solution was raised to room temperature gradually. Water was added to the reaction solution. The mixture was extracted with EtOAc. The extract was washed, dried and evaporated. The residue was purified by column chromatography on silica gel (CH2Cl2 --CH3OH) to give the title compound (62 mg) having the following physical data:

Workup

  1. stirringThe solution was stirred for 1 hr, while the temperature of the solution
  2. extractionThe mixture was extracted with EtOAc
  3. washThe extract was washed
  4. customdried
  5. customevaporated
  6. customThe residue was purified by column chromatography on silica gel (CH2Cl2 --CH3OH)

Sources & evidence

ORD record
ord-64a966da9ba54a38bdaceef62b918809
Source dataset
uspto-grants-1995_05
Patent number
US05411974

Reaction notes

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