Benzyl mercaptan → HCID 178512918, compound

HRID 1388962Notes

Reaction equation

HRID 1388962 reaction equation
[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@H:2]([C:10]([OH:12])=O)[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:9])[NH2:8].Cl.[CH2:24]([SH:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C1CCC(N=C=NC2CCCCC2)CC1>CN(C)C=O.C(OCC)(=O)C>[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@H:2]([C:10]([S:31][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:12])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:9])[NH2:8]

Participants

6

Reactant 3

HCID 7509Benzyl mercaptanHCID 10868DicyclohexylcarbodiimideHCID 178479461HCID 178479461, compound

Product 1

HCID 178512918HCID 178512918, compoundYield 124.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Z-Arg-OH.HCl (6 g, 8.7 mmoles) and benzyl mercaptan (4.2 ml, 17.4 mmoles) are dissolved in dimethylformamide (DMF) and cooled to 0° C. DCC (3.6 g, 8.7 mmoles), dissolved in DMF, is then added to the above reaction mixture, stirred at 0° C. for 30 minutes, then stirred overnight at room temperature. The precipitate formed is removed by filtration and the filtrate is concentrated under vacuum to yield an oil. This oily residue is dissolved in ethyl acetate and washed, successively, with 0.1 N HCl, 5% NaHCO3, and saturated aqueous NaCl. The organic layer is dried over anhydrous Na2SO4 and the solvent removed by evaporation. The crude product is purified by silica gel column, using a CHCl3 /methanol system, yielding 4.5 g of the product.

Workup

  1. additionis then added to the above reaction mixture
  2. stirringstirred overnight at room temperature
  3. customThe precipitate formed
  4. customis removed by filtration
  5. concentrationthe filtrate is concentrated under vacuum
  6. customto yield an oil
  7. washwashed
  8. dry with materialThe organic layer is dried over anhydrous Na2SO4
  9. customthe solvent removed by evaporation
  10. customThe crude product is purified by silica gel column

Sources & evidence

ORD record
ord-ed4503bac6db4a7aa68c5cc7002588ac
Source dataset
uspto-grants-1984_02
Patent number
US04434096

Reaction notes

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