Dichloromethane → HCID 178445903, compound

HRID 1607414Notes

Reaction equation

HRID 1607414 reaction equation
[CH2:1]([CH:8]([CH2:12][NH:13][C:14](=[O:26])[CH2:15][C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1)[C:9](O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.ClCCl.[NH2:42][C@H:43]([C:50]([NH:52][C@H:53]([CH:58]=[N:59][NH:60][C:61]([NH2:63])=[O:62])[CH2:54][CH:55]([CH3:57])[CH3:56])=[O:51])[CH2:44][C:45]1[N:49]=[CH:48][NH:47][CH:46]=1>CN(C)C=O.C(N(CC)CC)C>[CH2:1]([CH:8]([CH2:12][NH:13][C:14](=[O:26])[CH2:15][C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1)[C:9]([NH:42][C@H:43]([C:50]([NH:52][C@H:53]([CH:58]=[N:59][NH:60][C:61]([NH2:63])=[O:62])[CH2:54][CH:55]([CH3:57])[CH3:56])=[O:51])[CH2:44][C:45]1[N:49]=[CH:48][NH:47][CH:46]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 682631,1'-CarbonyldiimidazoleHCID 14600097(+/-)-2-Benzyl-3-(1-naphthylacetamido)propionic acidHCID 178445905HCID 178445905, compound

Product 1

HCID 178445903HCID 178445903, compoundYield 11.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 139 mg of (±)-2-benzyl-3-(1-naphthylacetamido)propionic acid and 65 mg of 1,1'-carbonyldiimidazole was added to 5 ml of dry dichloromethane, and the mixture was stirred for 1 hour at room temperature. The reaction mixture was added to a solution of 261 mg of L-histidyl-L-leucinal semicarbazone.2p-toluenesulfonic acid salt and 0.11 ml of triethylamine in 3 ml of dry N,N-dimethylformamide, and the mixture was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure, and a 5% aqueous sodium bicarbonate solution was added to the residue. The mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by preparative silica gel thin layer chromatography (developing solvent: lower layer of chloroform/methanol/water=8/3/1 by volume) to obtain 30 mg of N-[(±)-2-benzyl-3-(1-naphthylacetamido)propionyl]-L-histidyl-L-leucinal semicarbazone as a white powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiona 5% aqueous sodium bicarbonate solution was added to the residue
  3. extractionThe mixture was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by preparative silica gel thin layer chromatography (developing solvent: lower layer of chloroform/methanol/water=8/3/1 by volume)

Sources & evidence

ORD record
ord-416138056d044d7c85aaaf00378d909f
Source dataset
uspto-grants-1989_09
Patent number
US04863904

Reaction notes

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