4-Methylmorpholine → HCID 178427579, compound

HRID 647398Notes

Reaction equation

HRID 647398 reaction equation
[NH:1]([C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24])[C@H:2]([C:20]([OH:22])=O)[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:19])[NH:8][S:9]([C:12]1[CH:18]=[CH:17][C:15]([CH3:16])=[CH:14][CH:13]=1)(=[O:11])=[O:10].CN1CCOCC1.ClC(OCC)=O.[NH2:46][C@H:47]([C:56]([NH:58][C@H:59]([C:66]([NH:68][C@H:69]([C:71]([OH:73])=[O:72])[CH3:70])=[O:67])[CH2:60][O:61][C:62]([CH3:65])([CH3:64])[CH3:63])=[O:57])[CH2:48][C:49](=[O:55])[O:50][C:51]([CH3:54])([CH3:53])[CH3:52]>CN(C)C=O>[NH:1]([C:23]([O:25][CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)=[O:24])[C@H:2]([C:20]([NH:46][C@H:47]([C:56]([NH:58][C@H:59]([C:66]([NH:68][C@H:69]([C:71]([OH:73])=[O:72])[CH3:70])=[O:67])[CH2:60][O:61][C:62]([CH3:63])([CH3:64])[CH3:65])=[O:57])[CH2:48][C:49](=[O:55])[O:50][C:51]([CH3:52])([CH3:54])[CH3:53])=[O:22])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:19])[NH:8][S:9]([C:12]1[CH:18]=[CH:17][C:15]([CH3:16])=[CH:14][CH:13]=1)(=[O:10])=[O:11]

Participants

6

Reactant 4

HCID 79724-Methylmorpholine2×HCID 10928Ethyl chloroformateHCID 13371875HCID 13371875, compoundHCID 178427582HCID 178427582, compound

Product 1

HCID 178427579HCID 178427579, compoundYield 89.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
-5 °C

Procedure

In 290 ml of dimethylformamide is dissolved 16.2 g (35 millimoles) of Z-Arg(Tos)-OH, and 3.85 ml of N-methylmorpholine is added to the solution and the mixture is cooled to -5° C. Then, 3.35 ml of ethyl chloroformate is dropped to the mixture under agitation and the mixture is stirred for 15 minutes and is then mixed with a cooled liquid formed by suspending 15.5 g (38.5 millimoles) of H-Asp(OBut)-Ser(But)-Ala-OH (having a melting point of 122° to 133° C.) in 290 ml of dimethylformamide and adding 4.3 ml of N-methylmorpholine. The resulting mixture is stirred for 3 hours, and the insoluble substances are removed by filtration. The filtrate is concentrated under reduced pressure and solidification is effects by addition of ether to obtain 26.6 g of intended glassy Z-Arg(Tos)-Asp(OBut)-Ser(But)-Ala-OH (the yield being 90%).

Workup

  1. additionis added to the solution
  2. additionis then mixed with a cooled liquid
  3. customformed
  4. stirringThe resulting mixture is stirred for 3 hours
  5. customthe insoluble substances are removed by filtration
  6. concentrationThe filtrate is concentrated under reduced pressure and solidification
  7. additionby addition of ether

Sources & evidence

ORD record
ord-83b86c6e1dda476da0f1e387a6921d70
Source dataset
uspto-grants-1983_10
Patent number
US04407745

Reaction notes

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