Dichloromethane → HCID 178445899, compound

HRID 1607413Notes

Reaction equation

HRID 1607413 reaction equation
[C:1]1([CH2:11][NH:12][C:13]([CH:15]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:16](O)=[O:17])=[O:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.ClCCl.[NH2:41][C@H:42]([C:49]([NH:51][C@H:52]([CH:57]=[N:58][NH:59][C:60]([NH2:62])=[O:61])[CH2:53][CH:54]([CH3:56])[CH3:55])=[O:50])[CH2:43][C:44]1[N:48]=[CH:47][NH:46][CH:45]=1>CN(C)C=O.C(N(CC)CC)C>[C:1]1([CH2:11][NH:12][C:13]([CH:15]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:16]([NH:41][C@H:42]([C:49]([NH:51][C@H:52]([CH:57]=[N:58][NH:59][C:60]([NH2:62])=[O:61])[CH2:53][CH:54]([CH3:56])[CH3:55])=[O:50])[CH2:43][C:44]2[N:48]=[CH:47][NH:46][CH:45]=2)=[O:17])=[O:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 682631,1'-CarbonyldiimidazoleHCID 14600096(+/-)-2-(1-Naphthylmethylcarbamoyl)-3-phenylpropionic acidHCID 178445905HCID 178445905, compound

Product 1

HCID 178445899HCID 178445899, compoundYield 12.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 102 mg of (±)-2-(1-naphthylmethylcarbamoyl)-3-phenylpropionic acid and 50 mg of 1,1'-carbonyldiimidazole was added to 5 ml of dichloromethane, and the mixture was stirred for 40 minutes at room temperature. The reaction mixture was added to a solution of 202 mg of L-histidyl-L-leucinal semicarbazone.2p-toluenesulfonic acid salt and 0.09 ml of triethylamine in 3 ml of 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, dried 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 24 mg of N-[(±)-2-(1-naphthylmethylcarbamoyl)-3-phenylpropionyl]-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. customdried
  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-78f84b598104434f95eb0143dd5f708c
Source dataset
uspto-grants-1989_09
Patent number
US04863904

Reaction notes

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