4-Methylmorpholine → HCID 178512863, compound

HRID 1651086Notes

Reaction equation

HRID 1651086 reaction equation
[NH:1]([C:20]([O:22][CH2:23][CH:24]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:30]2[C:25]1=[CH:26][CH:27]=[CH:28][CH:29]=2)=[O:21])[C@@H:2]([C:10]([N:12]1[CH2:19][CH2:18][CH2:17][C@H:13]1[C:14](O)=[O:15])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1.[NH2:62][C@H:63]([C:71]([NH2:73])=[O:72])[CH2:64][CH2:65][CH2:66][NH:67][C:68](=[NH:70])[NH2:69].CN1CCOCC1>CN(C=O)C.CC(O)=O>[C:20]([NH:1][C@@H:2]([C:10]([N:12]1[CH2:19][CH2:18][CH2:17][C@H:13]1[C:14]([NH:62][C@H:63]([C:71]([NH2:73])=[O:72])[CH2:64][CH2:65][CH2:66][NH:67][C:68](=[NH:69])[NH2:70])=[O:15])=[O:11])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)([O:22][CH2:23][CH:24]1[C:25]2[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:31]2[C:36]1=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:21]

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 50916381Fmoc-D-Phe-ProHCID 178512843Argininamide

Product 1

HCID 178512863HCID 178512863, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

1.45 g of Fmoc-D-Phe-Pro (3 mmol) and 405 mg of HOBt were dissolved in 40 ml of DMF and, at 0oC, 630 mg of DCC were added, and then the mixture was stirred at 0oC for 30 minutes and at room temperature for 30 min. Then 880 mg of Arg-NH2 × 2 CH3COOH and 630 pl of NMM were added. After 12 hours, insolubles were filtered off, the DMF was evaporated off, and the oily residue was taken up chloroform. The organic phase was extracted by shaking three times with saturated sodium bicarbonate solution and three times with saturated sodium chloride solution, and was dried over sodium sulfate. After the chloroform had been evaporated off, a pure product was obtained.

Workup

  1. waitAfter 12 hours
  2. filtrationinsolubles were filtered off
  3. customthe DMF was evaporated off
  4. extractionThe organic phase was extracted
  5. stirringby shaking three times with saturated sodium bicarbonate solution and three times with saturated sodium chloride solution
  6. dry with materialwas dried over sodium sulfate
  7. customAfter the chloroform had been evaporated off
  8. customa pure product was obtained

Sources & evidence

ORD record
ord-598a8172a73b4892bbbeb7534d477b21
Source dataset
uspto-grants-1990_05
Patent number
US04927809

Reaction notes

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