1-Indanylacetic acid → 3-(2-indanylacetyl)-L-thioproline ethyl ester

HRID 1086265Notes

Reaction equation

HRID 1086265 reaction equation
[CH:1]1([CH2:10][C:11]([OH:13])=O)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.CCN=C=NCCCN(C)C.Cl.[CH2:26]([O:28][C:29](=[O:35])[C@@H:30]1[CH2:34][S:33][CH2:32][NH:31]1)[CH3:27]>C(Cl)Cl>[CH2:26]([O:28][C:29](=[O:35])[C@@H:30]1[CH:34]([C:11](=[O:13])[CH2:10][CH:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH2:3][CH2:2]2)[S:33][CH2:32][NH:31]1)[CH3:27]

Participants

5

Reactant 3

HCID 965011-Indanylacetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 13011878Ethyl (4R)-4-thiazolidinecarboxylate

Product 1

HCID 1317169173-(2-indanylacetyl)-L-thioproline ethyl esterYield 57.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1.4 g of 2-indanylacetic acid and 1.9 g of WSC.HCl were added to 15 ml of methylene chloride under ice-cooling. The mixture was stirred for 5 minutes at room temperature. After an addition of 1.3 g of L-thioproline ethyl ester dissolved in 10 ml of methylene chloride, the mixture was stirred for 5 hours. The reaction mixture was washed with water, diluted hydrochloric acid, and saturated sodium hydrogen carbonate in this order. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue thus obtained was purified by silica gel column chromatography to produce 1.45 g of 3-(2-indanylacetyl)-L-thioproline ethyl ester as a colorless oil (yield: 57%).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 5 hours
  3. washThe reaction mixture was washed with water, diluted hydrochloric acid, and saturated sodium hydrogen carbonate in this order
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue thus obtained
  7. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a430a8c68ecf419ba0434ab8f081b75b
Source dataset
uspto-grants-1991_07
Patent number
US05028604

Reaction notes

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