p-Toluenesulfonic acid → HCID 178425965, compound

HRID 647400Notes

Reaction equation

HRID 647400 reaction equation
[NH:1]([C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26])[C@H:2]([C:22](O)=[O:23])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:21])[NH:8][S:9]([C:12]1[C:19]([CH3:20])=[CH:18][C:16]([CH3:17])=[CH:15][C:13]=1[CH3:14])(=[O:11])=[O:10].CN1CCOCC1.ClC(OCC)=O.S(O)(C1C=CC(C)=CC=1)(=O)=O.[NH2:59][C@H:60]([C:65]([O:67][CH2:68][C:69]1[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=1)=[O:66])[CH2:61][CH:62]([CH3:64])[CH3:63]>O1CCCC1.CN(C)C=O>[NH:1]([C:25]([O:27][CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)=[O:26])[C@H:2]([C:22]([NH:59][C@H:60]([C:65]([O:67][CH2:68][C:69]1[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=1)=[O:66])[CH2:61][CH:62]([CH3:64])[CH3:63])=[O:23])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:21])[NH:8][S:9]([C:12]1[C:13]([CH3:14])=[CH:15][C:16]([CH3:17])=[CH:18][C:19]=1[CH3:20])(=[O:10])=[O:11]

Participants

8

Reactant 5

HCID 6101p-Toluenesulfonic acidHCID 79724-Methylmorpholine2×HCID 10928Ethyl chloroformateHCID 6451313Benzyl L-leucinateHCID 178425966HCID 178425966, compound

Product 1

HCID 178425965HCID 178425965, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-5 °C

Procedure

In 300 ml of tetrahydrofuran is dissolved 49.0 g (100 millimoles) of Z-Arg(Mts)-OH, and 11 ml of N-methylmorpholine is added to the solution and the mixture is stirred at -5° C. for 5 minutes. Then, 9.6 ml of ethyl chloroformate is added to the mixture, and a cooled solution of 39.4 g (100 millimoles) of Tos-OH.H-Leu-OBzl and 11 ml of N-methylmorpholine in dimethylformamide is added to the above mixture. The resulting mixture is stirred at -5° to 0° C. for 4 hours and concentrated under reduced pressure. The residue is dissolved in 700 ml of ethyl acetate, and the solution is washed with 0.1 N aqueous hydrochloric acid, 1 N aqueous NaHCO3 and water and concentrated under a reduced pressure to obtain 52 g of intended Z-Arg(Mts)-Leu-OBzl (the yield being 75%) like oil.

Workup

  1. additionis added to the solution
  2. stirringThe resulting mixture is stirred at -5° to 0° C. for 4 hours
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue is dissolved in 700 ml of ethyl acetate
  5. washthe solution is washed with 0.1 N aqueous hydrochloric acid, 1 N aqueous NaHCO3 and water
  6. concentrationconcentrated under a reduced pressure

Sources & evidence

ORD record
ord-74c89c7b90494f55ae7b4bbd804f5a52
Source dataset
uspto-grants-1983_10
Patent number
US04407745

Reaction notes

Loading…