Hydrochloric Acid → HCID 53935835, compound

HRID 2413723Notes

Reaction equation

HRID 2413723 reaction equation
[NH2:1][C@H:2]([C:4]([N:6]1[CH2:20][CH2:19][CH2:18][C@H:7]1[C:8]([N:10]1[CH2:17][CH2:16][CH2:15][C@H:11]1[C:12]([OH:14])=[O:13])=[O:9])=[O:5])[CH3:3].C(N(CC)CC)C.[CH2:28](Br)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.Cl.[C:37](=[S:39])=[S:38]>O.O1CCOCC1.C(OCC)(=O)C.O.O1CCOCC1>[CH2:28]([S:39][C:37]([NH:1][C@H:2]([C:4]([N:6]1[CH2:20][CH2:19][CH2:18][C@H:7]1[C:8]([N:10]1[CH2:17][CH2:16][CH2:15][C@H:11]1[C:12]([OH:14])=[O:13])=[O:9])=[O:5])[CH3:3])=[S:38])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 6348Carbon DisulfideHCID 7498Benzyl BromideHCID 8471TriethylamineHCID 1155826522049-75-8

Product 1

HCID 53935835HCID 53935835, compoundYield 51.9%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

L-alanyl-L-prolyl-L-proline (2.83 g, 10 m mole) was dissolved in water-dioxane (2:1, 15 ml), and triethyl amine (2.13 g, 21 m mole) was added thereto. To the solution, carbon disulfide (0.76 g, 10 m mole)-dioxane (5 ml) solution was added dropwise. After completion of the addition, the solution was stirred for 1 hour at room temperature. Thereafter, benzyl bromide (1.71 g, 10 m mole) was added thereto; and the mixture was stirred overnight at room temperature, and then water (100 ml) and ethyl acetate (150 ml) were added thereto. The solution was adjusted to pH2 with 1N hydrochloric acid while stirring vigorously. The ethyl acetate phase was separated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to give a glassy residue. The residue was recrystallized with ethyl acetate-n-hexane to give N-(benzylthio)thiocarbonyl-L-alanyl-L-prolyl-L-proline (2.33 g).

Workup

  1. additionAfter completion of the addition
  2. stirringand the mixture was stirred overnight at room temperature
  3. stirringwhile stirring vigorously
  4. customThe ethyl acetate phase was separated
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customto give a glassy residue
  8. customThe residue was recrystallized with ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-4b178bd143b341dd88b228cad05918a5
Source dataset
uspto-grants-1988_01
Patent number
US04719200

Reaction notes

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