Triethylamine → HCID 131718966, compound

HRID 1654535Notes

Reaction equation

HRID 1654535 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[CH2:10][C:11]([CH:13]1[S:17][CH2:16][NH:15][C@@H:14]1[C:18]([OH:20])=O)=[O:12].C(N(CC)CC)C.C(Cl)(=O)C(C)(C)C.[NH:35]1[CH2:41][CH2:40][CH2:39][C@H:36]1[CH2:37][OH:38]>C(Cl)Cl>[CH2:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:1][CH:2]1[CH2:10][C:11]([CH:13]1[S:17][CH2:16][NH:15][C@@H:14]1[C:18]([N:35]1[CH2:41][CH2:40][CH2:39][C@H:36]1[CH2:37][OH:38])=[O:20])=[O:12]

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 62493Pivaloyl chlorideHCID 640091L-ProlinolHCID 131718967HCID 131718967, compound

Product 1

HCID 131718966HCID 131718966, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(Indan-2-ylacetyl)-L-thioproline (11.7 g) and triethylamine (5.6 ml) were dissolved in 100 ml of methylene chloride, followed by dropwise addition of 4.95 g of pivaloyl chloride under agitation while cooling in ice for 15 minutes. Subsequently, 4.05 g of L-prolinol and 5.6 ml of triethylamine were added dropwise and stirred at room temperature for another one hour. The reaction solution were washed in 1N HCl, saturated aqueous solution of sodium bicarbonate and saturated sodium chloride solution, dried over anhydrous magnesium sulfate, followed by distillation of the solvent under reduced pressure. The resulting residue was purified by column chromatography to obtain 8.80 g of 1-[3-(indan-2-ylacetyl)-L-thioprolyl]-L-prolinol. Yield; 59%.

Workup

  1. temperaturewhile cooling in ice for 15 minutes
  2. washThe reaction solution were washed in 1N HCl
  3. dry with materialsaturated aqueous solution of sodium bicarbonate and saturated sodium chloride solution, dried over anhydrous magnesium sulfate
  4. distillationfollowed by distillation of the solvent under reduced pressure
  5. customThe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-a4374bf80634444ea03c13529615f835
Source dataset
uspto-grants-1995_04
Patent number
US05407950

Reaction notes

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