L-Phenylalanine → HCID 86739177, compound

HRID 2295511Notes

Reaction equation

HRID 2295511 reaction equation
[C:1]([S:4][CH2:5][CH2:6][C:7]([N:9]1[C@H:13]([C:14]([OH:16])=O)[CH2:12][S:11][C@@H:10]1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[OH:23])=[O:8])(=[O:3])[CH3:2].CN1CC[O:28]CC1.C(Cl)(=O)[O:32][CH2:33][CH:34]([CH3:36])C.N[C@H:40]([C:48](O)=O)[CH2:41][C:42]1C=CC=CC=1.C([N:53]([CH2:56][CH3:57])CC)C>C1COCC1>[C:1]([S:4][CH2:5][CH2:6][C:7]([N:9]1[C@H:13]([C:14]([N:53]([C:56]2[CH:57]=[CH:42][CH:41]=[CH:40][CH:48]=2)[C@H:34]([C:33]([OH:32])=[O:28])[CH3:36])=[O:16])[CH2:12][S:11][C@@H:10]1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[OH:23])=[O:8])(=[O:3])[CH3:2]

Participants

7

Reactant 5

HCID 6140L-PhenylalanineHCID 79724-MethylmorpholineHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 13316857HCID 13316857, compound

Product 1

HCID 86739177HCID 86739177, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the solution of 3.55 g of (2R,4R)-3-(S-acetyl-3-mercaptopropanoyl)-2-(2-hydroxyphenyl)-4-thiazolidinecarboxylic acid dissolved in 60l ml of THF 1.0 g of N-methylmorpholine is added. To the reaction mixture 1.4 g of isobutyl chlorocarbonate is added at a temperature of -15° to -10° C. The suspension obtained by stirring it for 1 hour is added to 60 ml of the aqueous solution of 3.38 g of L-phenylalanine and 2.0 g of triethylamine with stirring under ice-cooling. After stirring it under ice-cooling for 10 minutes and at room temperature for an additional 10 minutes, the solution is concentrated in vacuo. The concentrate is washed with two 100-ml portions of ether, acidified with conc. hydrochloric acid, and extracted with ethyl acetate. The organic layer is washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated in vacuo to give 4.8 g (96%) of the titled compound.

Workup

  1. additionis added
  2. customThe suspension obtained
  3. stirringwith stirring under ice-
  4. temperaturecooling
  5. stirringAfter stirring it under ice-
  6. concentrationthe solution is concentrated in vacuo
  7. washThe concentrate is washed with two 100-ml portions of ether
  8. extractionextracted with ethyl acetate
  9. washThe organic layer is washed with saturated aqueous sodium chloride solution
  10. dry with materialdried over anhydrous magnesium sulfate
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2796d33ec2164c5f8496066834a37945
Source dataset
uspto-grants-1984_01
Patent number
US04425333

Reaction notes

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