Hydrochloric Acid → HCID 131717770, compound

HRID 2082228Notes

Reaction equation

HRID 2082228 reaction equation
[NH:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3][C:4]([OH:6])=O.Cl.[NH2:15][C@H:16]([C:20]([NH:22][C@@H:23]([C:36]([NH:38][C@H:39]([C:47]([N:49]([CH2:51][C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)[CH3:50])=[O:48])[CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)=[O:37])[CH2:24][C:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[N:27]([CH:34]=[O:35])[CH:26]=1)=[O:21])[C@@H:17]([CH3:19])[OH:18].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C>[NH:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3][C:4]([NH:15][C@H:16]([C:20]([NH:22][C@@H:23]([C:36]([NH:38][C@H:39]([C:47]([N:49]([CH2:51][C:52]1[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=1)[CH3:50])=[O:48])[CH2:40][C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1)=[O:37])[CH2:24][C:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[N:27]([CH:34]=[O:35])[CH:26]=1)=[O:21])[C@@H:17]([CH3:19])[OH:18])=[O:6]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 76809N-((1,1-dimethylethoxy)carbonyl)-beta-alanineHCID 101632290HCID 101632290, compound

Product 1

HCID 131717770HCID 131717770, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Boc-βAla-OH (0.19 g), HCl.H-Thr-D-Trp(CHO)-Phe-NMeBzl (0.62 g) and HOBT (0.14 g) were dissolved in DMF (10 ml). To this solution was added WSC (0.18 ml) under ice cooling and the mixture was stirred for four hours at room temperature. After evaporation and extraction with ethyl acetate, the organic layer was washed successively with water, 2% sodium hydrogencarbonate solution, water, 2% hydrochloric acid, water and saturated sodium chloride solution, and dried over magnesium sulfate. The evaporated residue was crystallized from a mixed solvent of ethanol and water. Filtration and drying gave Boc-βAla-Thr-D-Trp(CHO)-Phe-NMeBzl (0.66 g).

Workup

  1. customAfter evaporation and extraction with ethyl acetate
  2. washthe organic layer was washed successively with water, 2% sodium hydrogencarbonate solution, water, 2% hydrochloric acid, water and saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. customThe evaporated residue was crystallized from a mixed solvent of ethanol and water
  5. filtrationFiltration
  6. customdrying

Sources & evidence

ORD record
ord-c75147878f5a40b9b15c5dd481cc41e0
Source dataset
uspto-grants-1993_02
Patent number
US05187156

Reaction notes

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