Ethylmorpholine → HCID 15600423, compound

HRID 1111649Notes

Reaction equation

HRID 1111649 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][C:13]([OH:15])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1.FC(F)(F)C(O)=O.[CH3:48][O:49][C:50](=[O:71])[C@H:51]([CH2:64][C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1)[NH:52][C:53](=[O:63])[C@H:54]([CH2:56][C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1)[NH2:55].C(N1CCOCC1)C>CN(C)C=O>[CH3:48][O:49][C:50](=[O:71])[C@H:51]([CH2:64][C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1)[NH:52][C:53](=[O:63])[C@H:54]([CH2:56][C:57]1[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=1)[NH:55][C:13](=[O:15])[CH2:12][NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10]

Participants

7

Reactant 5

HCID 7525EthylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 14349BenzyloxycarbonylglycineHCID 757711-HydroxybenzotriazoleHCID 70614783HCID 70614783, compound

Product 1

HCID 15600423HCID 15600423, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred, cooled (0° C.) solution of benzyloxycarbonylglycine (955mg, 4.5 mmole) and 1-hydroxybenzotriazole (1.2 g, 9 mmole) in dimethylformamide (15 ml) is added dicyclohexylcarbodiimide (1.03 g, 5 mmole). The mixture is stirred for 1 hour at 0° C. A cooled solution of phenylalanyl-phenylalanine methyl ester trifluoroacetate (2.0 g, 4.5 mmoles, described in U.S. Pat. No. 3,917,578, noted above) in dimethylformamide (20 ml) and N-ethyl morpholine (0.58 ml) is added and the mixture is stirred overnight at room temperature. The mixture is filtered and the filtrate is evaporated. The residue is dissolved in ethyl acetate (100 ml) and the solution is filtered. The filtrate is washed with 10% aqueous citric acid solution, saturated sodium chloride solution, saturated sodium bicarbonate solution and saturated sodium chloride solution. The solution is dried over magnesium sulfate (anhydrous) and evaporated. The residue is crystalized from ethyl acetate-petroleum ether (30°-60°) to give the title compound as crystals, mp 122°-124° C.

Workup

  1. stirringthe mixture is stirred overnight at room temperature
  2. filtrationThe mixture is filtered
  3. customthe filtrate is evaporated
  4. dissolutionThe residue is dissolved in ethyl acetate (100 ml)
  5. filtrationthe solution is filtered
  6. washThe filtrate is washed with 10% aqueous citric acid solution, saturated sodium chloride solution, saturated sodium bicarbonate solution and saturated sodium chloride solution
  7. dry with materialThe solution is dried over magnesium sulfate (anhydrous)
  8. customevaporated
  9. customThe residue is crystalized from ethyl acetate-petroleum ether (30°-60°)

Sources & evidence

ORD record
ord-9a1bb37fafe64d3cafae6d52c174574c
Source dataset
uspto-grants-1978_10
Patent number
US04118380

Reaction notes

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