Triethylamine → HCID 15170720, compound

HRID 486884

Reaction equation

HRID 486884 reaction equation
[SH:1][C:2]([CH3:13])([CH3:12])[C:3]([NH:5][C@H:6]([C:9](O)=[O:10])[CH2:7][SH:8])=[O:4].[CH:14]1([N:20]=[C:21]=NC2CCCCC2)CCCCC1.Cl.CNC.C(N(CC)CC)C>C(Cl)Cl.CO.C(OC(=O)C)C>[CH3:14][N:20]([CH3:21])[C:9](=[O:10])[C@H:6]([CH2:7][SH:8])[NH:5][C:3](=[O:4])[C:2]([SH:1])([CH3:13])[CH3:12]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 10868DicyclohexylcarbodiimideHCID 656604Bucillamine

Product 1

HCID 15170720HCID 15170720, compoundYield 98.9%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of N-(2-mercapto-2-methylpropionyl)-L-cysteine (1.0 g) in methylene chloride(4 ml), dicyclohexylcarbodiimide (0.5 g) dissolved in methylene chloride(4 ml) was added dropwise. After the addition, the reaction mixture was stirred for 30 minutes under ice cooling and for 1 hour at room temperature. Dimethylamine hydrochloride(0.2 g) and triethylamine(0.4 ml) dissolved in a mixture of methylene chloride (2 ml) and methanol(1 ml) was added dropwise under ice-cooling. The reaction mixture was stirred for 15 minutes under ice-cooling and 3 hours at room temperature. To the reaction mixture, ethylacetate was added and filtered. The organic layer was washed with water and concentrated in vacuo. The oily residue was purified by a silica gel column chromatography to give 0.6 g(50%) of the titled compound.

Workup

  1. additionwas added dropwise
  2. additionAfter the addition
  3. additionwas added dropwise under ice-
  4. temperaturecooling
  5. stirringThe reaction mixture was stirred for 15 minutes under ice-
  6. temperaturecooling and 3 hours at room temperature
  7. filtrationfiltered
  8. washThe organic layer was washed with water
  9. concentrationconcentrated in vacuo
  10. customThe oily residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-327165254db84b20a3c597fffea4a873
Source dataset
uspto-grants-1994_03
Patent number
US05292926

Linked notes

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