Ethylmorpholine → HCID 53789352, compound

HRID 1111652Notes

Reaction equation

HRID 1111652 reaction equation
[CH3:1][O:2][C:3](=[O:43])[C@H:4]([CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[NH:5][C:6](=[O:35])[C@H:7]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[NH:8][C:9](=[O:27])[C@H:10]([CH2:23][C:24](=[O:26])[NH2:25])[NH:11][C:12](=[O:22])[CH2:13][NH:14]C(OC(C)(C)C)=O.C(N1CCOCC1)C.ClC1C(O[C:60](=[S:82])[CH2:61][CH2:62][C:63]([C:76]2[CH:81]=[CH:80][CH:79]=[CH:78][CH:77]=2)([C:70]2[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=2)[C:64]2[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=2)=C(Cl)C(Cl)=C(Cl)C=1Cl>FC(F)(F)C(O)=O.CN(C)C=O>[CH3:1][O:2][C:3](=[O:43])[C@H:4]([CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[NH:5][C:6](=[O:35])[C@H:7]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[NH:8][C:9](=[O:27])[C@H:10]([CH2:23][C:24](=[O:26])[NH2:25])[NH:11][C:12](=[O:22])[CH2:13][NH:14][C:60](=[S:82])[CH2:61][CH2:62][C:63]([C:70]1[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=1)([C:64]1[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=1)[C:76]1[CH:77]=[CH:78][CH:79]=[CH:80][CH:81]=1

Participants

6

Reactant 3

HCID 7525EthylmorpholineHCID 54166524HCID 54166524, compoundHCID 54434155HCID 54434155, compound

Product 1

HCID 53789352HCID 53789352, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of t-butoxycarbonyl-glycyl-asparaginyl-phenylalanyl-phenylalanine methyl ester (0.525 g, 0.879 mmole, described in Example 4) in trifluoroacetic acid (10 ml) is stirred at 0° C. for 90 minutes and evaporated. The residue is dissolved in methanol (1 ml) and diethyl ether (100 ml) is added. The precipitate is collected and dried. A solution of the precipitate, N-ethylmorpholine (0.11 ml, 0.85 mmole) and 3-tritylthiopropionic acid pentachlorophenyl ester (0.556 g, 0.935 mmole) in dimethylformamide (25 ml) is stirred at 0° C. for 1 hour and at 25° C. for 20 hours and evaporated. The residue is triturated with methanol and the precipitate is dried to give the title compound as a powder, mp 234°-236.5° C.

Workup

  1. customevaporated
  2. dissolutionThe residue is dissolved in methanol (1 ml)
  3. additiondiethyl ether (100 ml) is added
  4. customThe precipitate is collected
  5. customdried
  6. customevaporated
  7. customThe residue is triturated with methanol
  8. customthe precipitate is dried

Sources & evidence

ORD record
ord-8e0830ca757b4c4383eacd2652fa07ac
Source dataset
uspto-grants-1978_10
Patent number
US04118380

Reaction notes

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