4-Methylmorpholine → HCID 18659599, compound

HRID 1608510Notes

Reaction equation

HRID 1608510 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:17]([NH:19][C@H:20]([C:25]([OH:27])=O)[CH2:21][CH2:22][CH2:23][CH3:24])=[O:18])[CH2:13][CH:14]([CH3:16])[CH3:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:28]N1CCOCC1.ClC(OCC)=O.[N+](=C)=[N-]>C1COCC1.C(OCC)C>[C:25]([CH:20]([NH:19][C:17](=[O:18])[C@H:12]([CH2:13][CH:14]([CH3:15])[CH3:16])[NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])[CH2:21][CH2:22][CH2:23][CH3:24])(=[O:27])[CH3:28]

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 9550DiazomethaneHCID 10928Ethyl chloroformateHCID 15284423HCID 15284423, compound

Product 1

HCID 18659599HCID 18659599, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

In 150 g of anhydrous THF were dissolved 5.4 g of N-benzyloxycarbonyl-L-leucyl-L-norleucine prepared in the same manner as in Example 1-(b) and 3.4 ml of N-methylmorpholine, and 1.6 g of ethyl chloroformate was added thereto under ice-cooling, followed by stirring at 0° C. for 30 minutes. The reaction mixture was added to an excess diazomethane solution in diethyl ether, and the solution was allowed to stand at 0° C. for 1 hour. The solvent was removed by distillation under reduced pressure, and the residue was purified by medium-pressure column chromatography on silica gel to obtain 4.0 g of the titled compound as a colorless crystal.

Workup

  1. temperatureunder ice-cooling
  2. waitto stand at 0° C. for 1 hour
  3. customThe solvent was removed by distillation under reduced pressure
  4. customthe residue was purified by medium-pressure column chromatography on silica gel

Sources & evidence

ORD record
ord-05280ccf94194cc7b10f471d585a4ca8
Source dataset
uspto-grants-1995_03
Patent number
US05395824

Reaction notes

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