p-Toluenesulfonic acid → HCID 15755271, compound

HRID 2082219Notes

Reaction equation

HRID 2082219 reaction equation
[NH:1]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C@@H:2]([C:15](O)=[O:16])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]([CH:13]=[O:14])[CH:5]=1.CC1C=CC(S(O)(=O)=O)=CC=1.[NH2:36][C@H:37]([C:45]([O:47][CH2:48][C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)=[O:46])[CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>C(Cl)Cl.CN(C=O)C>[NH:1]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C@@H:2]([C:15]([NH:36][C@H:37]([C:45]([O:47][CH2:48][C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)=[O:46])[CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:16])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]([CH:13]=[O:14])[CH:5]=1

Participants

8

Reactant 5

HCID 6101p-Toluenesulfonic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 736312Benzyl 3-phenyl-L-alaninateHCID 7021874Boc-D-Trp(For)-OH

Product 1

HCID 15755271HCID 15755271, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Boc-D-Trp(CHO)-OH (2.99 g), TsOH.H-Phe-OBzl (3.85 g, and HOBT (1.22 g) were dissolved in a mixed solvent of methylene chloride (60 ml) and DMF (15 ml). To this solution was added WSC (1.53 g) under ice cooling, and the reaction mixture was stirred for 3 hours at the same temperature. The reaction mixture was concentrated and extracted with ethyl acetate. The organic layer was washed successively with diluted sodium hydrogencarbonate solution (twice), water, 0.5N hydrochloric acid, and saturated sodium chloride solution, and dried over magnesium sulfate. After concentration, the residue was crystallized from a mixture of ethyl acetate and diisopropyl ether (1:1), which was filtered, washed with diisopropyl ether, and dried to give Boc-D-Trp(CHO)-Phe-OBzl (4.95 g).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed successively with diluted sodium hydrogencarbonate solution (twice), water, 0.5N hydrochloric acid, and saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationAfter concentration
  6. customthe residue was crystallized from a mixture of ethyl acetate and diisopropyl ether (1:1), which
  7. filtrationwas filtered
  8. washwashed with diisopropyl ether
  9. customdried

Sources & evidence

ORD record
ord-e54d37dc2c78445ca184ffd9ab28b01b
Source dataset
uspto-grants-1993_02
Patent number
US05187156

Reaction notes

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