Hydrochloric Acid → HCID 14999583, compound

HRID 2082220Notes

Reaction equation

HRID 2082220 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.Cl.[NH2:26][C@H:27]([C:35]([N:37]([CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[CH3:38])=[O:36])[CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C>[NH:1]([C:18]([O:20][C:21]([CH3:24])([CH3:22])[CH3:23])=[O:19])[C@@H:2]([C:15]([NH:26][C@H:27]([C:35]([N:37]([CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[CH3:38])=[O:36])[CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=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

7

Reactant 5

HCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 7021874Boc-D-Trp(For)-OHHCID 14999586HCID 14999586, compound

Product 1

HCID 14999583HCID 14999583, compoundYield 86.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Boc-D-Trp(CHO)-OH (3.26 g), HCl.H-Phe-NMeBzl (2.99 g) and HOBT (1.32 g) were dissolved in DMF (40 ml). To this solution was added WSC under ice cooling. The reaction mixture was stirred for an hour at this temperature and for additional an hour at room temperature. After evaporation and extraction with ethyl acetate, the organic layer was washed successively with diluted sodium hydrogencarbonate solution, water, 0.5N hydrochloric acid, and sodium chloride solution and dried over magnesium sulfate. The evaporated residue was crystallized from a mixed solvent of ethyl acetate and diisopropyl ether (3:4) (35 ml) with seeding. The crystals were collected by filtration after addition of diisopropyl ether (55 ml) and dried to give Boc-D-Trp(CHO)-Phe-NMeBzl (4.96 g).

Workup

  1. customAfter evaporation and extraction with ethyl acetate
  2. washthe organic layer was washed successively with diluted sodium hydrogencarbonate solution, water, 0.5N hydrochloric acid, and sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. customThe evaporated residue was crystallized from a mixed solvent of ethyl acetate and diisopropyl ether (3:4) (35 ml) with seeding
  5. filtrationThe crystals were collected by filtration
  6. additionafter addition of diisopropyl ether (55 ml)
  7. customdried

Sources & evidence

ORD record
ord-009c1acfc2c947998a7f8fc89f4195cd
Source dataset
uspto-grants-1993_02
Patent number
US05187156

Reaction notes

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