1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 131716919, compound

HRID 1086268Notes

Reaction equation

HRID 1086268 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH:2]1[CH2:11][C:12]([OH:14])=O.CCN=C=NCCCN(C)C.Cl.[CH2:27]([O:29][C:30](=[O:36])[C@@H:31]1[CH2:35][S:34][CH2:33][NH:32]1)[CH3:28]>C(Cl)Cl>[CH2:27]([O:29][C:30](=[O:36])[C@@H:31]1[CH:35]([C:12](=[O:14])[CH2:11][CH:2]2[CH2:3][CH2:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH2:1]2)[S:34][CH2:33][NH:32]1)[CH3:28]

Participants

5

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 100127392-(1,2,3,4-tetrahydronaphthalen-2-yl)acetic acidHCID 13011878Ethyl (4R)-4-thiazolidinecarboxylate

Product 1

HCID 131716919HCID 131716919, compoundYield 68.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 2.85 g of 1,2,3,4-tetrahydronaphthalen-2-ylacetic acid and 13.45 g of WSC.HCl was added 45 ml of methylene chloride under ice-cooling. The mixture was stirred for 5 minutes at room temperature. To this was added a solution of 2.4 g of L-thioproline ethyl ester in 7 ml of methylene chloride at room temperature, and the mixture was stirred for a further 18 hours at the same temperature. 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 3.4 g of 3-(1,2,3,4-tetrahydronaphthalen-2-ylacetyl)-L-thioproline ethyl ester as a colorless oil (yield: 68%).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for a further 18 hours at the same temperature
  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-a66faf0c329b428184a153c0d46eec24
Source dataset
uspto-grants-1991_07
Patent number
US05028604

Reaction notes

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