L-Prolinol → HCID 131718966, compound

HRID 1654533Notes

Reaction equation

HRID 1654533 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].[NH:21]1[CH2:27][CH2:26][CH2:25][C@H:22]1[CH2:23][OH:24].CCN=C=NCCCN(C)C.Cl>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:21]1[CH2:27][CH2:26][CH2:25][C@H:22]1[CH2:23][OH:24])=[O:20])=[O:12]

Participants

5

Reactant 3

HCID 640091L-ProlinolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 131718967HCID 131718967, compound

Product 1

HCID 131718966HCID 131718966, compoundYield 42.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(Indan-2-ylacetyl)-L-thioproline (4.40 g) and L-prolinol (1.53 g) were dissolved in 150 ml of methylene chloride, followed by addition of 2.90 g of WSC-HCl under agitation while cooling in ice and subsequent agitation for-another 30 minutes at room temperature. The reaction solution was washed sequentially in 5 HCl, saturated aqueous solution of sodium bicarbonate, saturated aqueous sodium chloride solution, followed by drying over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by column chromatography to obtain 2.40 g of 1-[3-(indan-2-yl-acetyl)-L-thioprolyl]-L-prolinol. Yield; 42%.

Workup

  1. temperaturewhile cooling in ice
  2. washThe reaction solution was washed sequentially in 5 HCl, saturated aqueous solution of sodium bicarbonate, saturated aqueous sodium chloride solution
  3. dry with materialby drying over anhydrous magnesium sulfate
  4. distillationAfter distilling off the solvent under reduced pressure
  5. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-17838cae35d0458cb3ae4f96f9fac140
Source dataset
uspto-grants-1995_04
Patent number
US05407950

Reaction notes

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