Hydrochloric Acid → HCID 178501379, compound

HRID 329546Notes

Reaction equation

HRID 329546 reaction equation
[NH:1]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C@H:2]([C:20]([OH:22])=O)[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:19])[NH:8][S:9]([C:12]1[CH:18]=[CH:17][C:15]([CH3:16])=[CH:14][CH:13]=1)(=[O:11])=[O:10].C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1.CCN(C(C)C)C(C)C.Cl.[NH2:57][C@H:58]([C:74]([O:76][CH3:77])=[O:75])[CH2:59][C:60]1[CH:65]=[CH:64][C:63]([O:66][CH2:67][C:68]2[CH:73]=[CH:72][CH:71]=[CH:70][CH:69]=2)=[CH:62][CH:61]=1>CN(C=O)C>[NH:1]([C:23]([O:25][C:26]([CH3:29])([CH3:27])[CH3:28])=[O:24])[C@H:2]([C:20]([NH:57][C@H:58]([C:74]([O:76][CH3:77])=[O:75])[CH2:59][C:60]1[CH:61]=[CH:62][C:63]([O:66][CH2:67][C:68]2[CH:69]=[CH:70][CH:71]=[CH:72][CH:73]=2)=[CH:64][CH:65]=1)=[O:22])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:19])[NH:8][S:9]([C:12]1[CH:18]=[CH:17][C:15]([CH3:16])=[CH:14][CH:13]=1)(=[O:10])=[O:11]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 83767L-Ornithine, N2-[(1,1-dimethylethoxy)carbonyl]-N5-[imino[[(4-methylphenyl)sulfonyl]amino]methyl]-HCID 199401P,P-Diphenylphosphinic azideHCID 6999558H-Tyr(Bzl)-OMe

Product 1

HCID 178501379HCID 178501379, compoundYield 169.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Dipeptide Boc-Arg(Tos)-Tyr(Bzl)-OCH3 : A solution of Boc-Arg(Tos)-OH (2.14 g, 5 mmol) and DPPA (1.37 g, 5 mmol) in DMF (100 mL) was cooled to -5° C. DIEA (2.6 mL, 15 mmol) and HCl.H-Tyr(Bzl)-OCH3 (1.44 g, 4.5 mmol) were added, each in one portion, to the cooled solution. The solution was stirred at -10° C. for 2h, allowed to stand at 4° C. for 18h, and then evaporated to dryness. The residue was dissolved in EtOAc (75 mL). The solution was washed sequentially with H2O, 1N HCl, 5% aqueous NaHCO3 and H2O, dried, and evaporated to dryness. The residue was dissolved in EtOAc. Addition of Et2O caused an oil to separate from the solution. The mixture was cooled (0° C.) and triturated. The solvent phase of the mixture was removed by decantation. Et2O was added to the residue. After warming the mixture, the preceding trituration and decantation treatment was repeated. Finally, the product was dried under reduced pressure to yield Boc-Arg(Tos)-Tyr(Bzl)-OCH3 (5.3 g).

Workup

  1. customevaporated to dryness
  2. dissolutionThe residue was dissolved in EtOAc (75 mL)
  3. washThe solution was washed sequentially with H2O, 1N HCl, 5% aqueous NaHCO3 and H2O
  4. customdried
  5. customevaporated to dryness
  6. dissolutionThe residue was dissolved in EtOAc
  7. additionAddition of Et2O
  8. customto separate from the solution
  9. customtriturated
  10. customThe solvent phase of the mixture was removed by decantation
  11. additionEt2O was added to the residue
  12. temperatureAfter warming the mixture
  13. customFinally, the product was dried under reduced pressure

Sources & evidence

ORD record
ord-f2111941977b4e8bba80ec896ac8183c
Source dataset
uspto-grants-1990_01
Patent number
US04891358

Reaction notes

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