p-Toluenesulfonic acid → HCID 178427522, compound

HRID 652369Notes

Reaction equation

HRID 652369 reaction equation
[NH:1]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@H:2]([C:10]([OH:12])=O)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[NH2:20][C@H:21]([C:29]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30])[CH2:22][CH2:23][CH2:24][NH:25][C:26](=[NH:28])[NH2:27].[S:39](O)([C:42]1[CH:48]=[CH:47][C:45]([CH3:46])=[CH:44][CH:43]=1)(=[O:41])=[O:40].C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.CCCCCC.C(OCC)(=O)C>[NH:1]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@H:2]([C:10]([NH:20][C@H:21]([C:29]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30])[CH2:22][CH2:23][CH2:24][NH:25][C:26](=[NH:27])[NH:28][S:39]([C:42]1[CH:48]=[CH:47][C:45]([CH3:46])=[CH:44][CH:43]=1)(=[O:41])=[O:40])=[O:12])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

8

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 757711-HydroxybenzotriazoleHCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-HCID 178512913HCID 178512913, compound

Product 1

HCID 178427522HCID 178427522, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

Boc-Phe-OH (4 g, 15 mmole), H-Arg-OBzl.TosOH (8.9 g, 15 mmole) and HOBt (2.1 g, 15.75 mmole) were dissolved in DMF (25 ml), and WSCI (12.9 ml, 15.75 mmole) was added dropwise thereto while cooling, and the thus-obtained mixture (pH=4) was stirred overnight. To the reaction solution, AcOEt (300 ml) was added thereto, and the solution was washed with 1N HCl, water and 5% NaHCO3 and water, in order, and dried with Na2SO4 . AcOEt was distilled off under reduced pressure, and the thus-obtained residue was treated with ethyl acetate, ether, and n-hexane to give an oily substance. The substance was obtained by decantation and treated with ethyl acetate and hexane to give precipitates of the object product (6.89 g, 60%).

Workup

  1. additionWSCI (12.9 ml, 15.75 mmole) was added dropwise
  2. temperaturewhile cooling
  3. washthe solution was washed with 1N HCl, water and 5% NaHCO3 and water, in order
  4. dry with materialdried with Na2SO4
  5. distillationAcOEt was distilled off under reduced pressure
  6. additionthe thus-obtained residue was treated with ethyl acetate, ether, and n-hexane
  7. customto give an oily substance
  8. customThe substance was obtained by decantation
  9. customto give
  10. customprecipitates of the object product (6.89 g, 60%)

Sources & evidence

ORD record
ord-33c46450a8d148c4a62aa1d1f8fbf767
Source dataset
uspto-grants-1987_06
Patent number
US04670540

Reaction notes

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