Hydrochloric Acid → HCID 101632281, compound

HRID 2082223Notes

Reaction equation

HRID 2082223 reaction equation
[NH:1]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C@H:2]([C:6]([OH:8])=O)[C@@H:3]([CH3:5])[OH:4].Cl.[NH2:17][C@@H:18]([C:31]([NH:33][C@H:34]([C:42]([N:44]([CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)[CH3:45])=[O:43])[CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:32])[CH2:19][C:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:22]([CH:29]=[O:30])[CH:21]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C>[NH:1]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C@H:2]([C:6]([NH:17][C@@H:18]([C:31]([NH:33][C@H:34]([C:42]([N:44]([CH2:46][C:47]1[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=1)[CH3:45])=[O:43])[CH2:35][C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)=[O:32])[CH2:19][C:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:22]([CH:29]=[O:30])[CH:21]=1)=[O:8])[C@@H:3]([CH3:5])[OH:4]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 2724766N-tert-Butoxycarbonyl-L-threonineHCID 14999588HCID 14999588, compound

Product 1

HCID 101632281HCID 101632281, compoundYield 94.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Boc-Thr-OH (1.23 g), HCl.H-D-Trp(CHO)-Phe-NMeBzl (3.0 g) and HOBT (0.757 g) were dissolved in DMF (40 ml). To this solution was added WSC (887 mg) under ice cooling and the mixture was stirred for 1.5 hours at the same temperature and overnight at room temperature. After evaporation and extraction with ethyl acetate, the organic layer was washed successively with water, 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 (1:1) (10 ml) with seeding and the crystals were washed out by addition of diisopropyl ether (30 ml) and dried to give Boc-Thr-D-Trp(CHO)-Phe-NMeBzl (3.64 g).

Workup

  1. customAfter evaporation and extraction with ethyl acetate
  2. washthe organic layer was washed successively with water, 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 (1:1) (10 ml) with seeding
  5. washthe crystals were washed out by addition of diisopropyl ether (30 ml)
  6. customdried

Sources & evidence

ORD record
ord-70220d84da8e45e0bfb49a1803f02a45
Source dataset
uspto-grants-1993_02
Patent number
US05187156

Reaction notes

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