4-Methylmorpholine → HCID 178445898, compound

HRID 1607411Notes

Reaction equation

HRID 1607411 reaction equation
[CH2:1]([CH:8]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:9]([OH:11])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:31][C@H:32]([C:39]([NH:41][C@H:42]([CH:47]=[N:48][NH:49][C:50]([NH2:52])=[O:51])[CH2:43][CH:44]([CH3:46])[CH3:45])=[O:40])[CH2:33][C:34]1[N:38]=[CH:37][NH:36][CH:35]=1.CN1CCOCC1>CN(C)C=O.ClCCl>[CH2:12]([CH:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:9]([NH:31][C@H:32]([C:39]([NH:41][C@H:42]([CH:47]=[N:48][NH:49][C:50]([NH2:52])=[O:51])[CH2:43][CH:44]([CH3:46])[CH3:45])=[O:40])[CH2:33][C:34]1[N:38]=[CH:37][NH:36][CH:35]=1)=[O:11])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 64800Benzenepropanoic acid, alpha-(phenylmethyl)-HCID 682631,1'-CarbonyldiimidazoleHCID 178445905HCID 178445905, compound

Product 1

HCID 178445898HCID 178445898, compoundYield 30.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 240 mg of 2-benzyl-3-phenylpropionic acid and 170 mg of 1,1'-carbonyldiimidazole was added to 10 ml of dry dichloromethane, and the mixture was stirred for 30 minutes at room temperature. The reaction mixture was added to a solution of 650 mg of L-histidyl-L-leucinal semicarbazone.2p-toluenesulfonic acid salt and 200 mg of N-methylmorpholine in 10 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, and the organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel flash column chromatography (eluent: dichloromethane/methanol=10/1 by volume) to obtain 162 mg of N-(2-benzyl-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. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel flash column chromatography (eluent: dichloromethane/methanol=10/1 by volume)

Sources & evidence

ORD record
ord-bd30c918bb404affa131e936175b07fe
Source dataset
uspto-grants-1989_09
Patent number
US04863904

Reaction notes

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