Ethylmorpholine → HCID 178476723, compound

HRID 1883483Notes

Reaction equation

HRID 1883483 reaction equation
[B-](F)(F)(F)F.CC[O:8][C:9]([C:11](C#N)=NOC(N(C)C)=[N+](C)C)=[O:10].Cl.[C:24]([C:27]1[CH:32]=[CH:31][C:30]([CH2:33][CH:34]([CH:48]2[CH2:53][CH2:52][CH2:51][CH2:50][CH2:49]2)[C:35]([NH:37][C@@H:38]([CH:42]2[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]2)[C:39](O)=[O:40])=[O:36])=[CH:29][CH:28]=1)(=[NH:26])[NH2:25].Cl.Cl.[CH2:56]([NH:64][C:65](=[O:75])[C@@H:66]([NH2:74])[CH2:67][CH2:68][CH2:69][NH:70][C:71]([NH2:73])=[NH:72])[CH2:57][C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1.C(N1CCOCC1)C>CN(C)C=O>[C:9]([OH:10])(=[O:8])[CH3:11].[CH2:56]([NH:64][C:65](=[O:75])[C@@H:66]([NH:74][C:39](=[O:40])[CH:38]([NH:37][C:35](=[O:36])[CH:34]([CH:48]1[CH2:49][CH2:50][CH2:51][CH2:52][CH2:53]1)[CH2:33][C:30]1[CH:31]=[CH:32][C:27]([C:24](=[NH:25])[NH2:26])=[CH:28][CH:29]=1)[CH:42]1[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]1)[CH2:67][CH2:68][CH2:69][NH:70][C:71]([NH2:73])=[NH:72])[CH2:57][C:58]1[CH:59]=[CH:60][CH:61]=[CH:62][CH:63]=1

Participants

6

Reactant 4

HCID 7525EthylmorpholineHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 131724490HCID 131724490, compoundHCID 178478818HCID 178478818, compound

Product 1

HCID 178476723HCID 178476723, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
22 °C

Procedure

At 4° C. TOTU (48 mg, 0.14 mmol) was added to a solution of [3-(4-carbamimidoyl-phenyl)-2-(R,S)-cyclohexyl-propionylamino]-(S)-cyclohexyl-acetic acid hydrochloric acid salt (60 mg, 0.14 mmol), (S)-2-amino-5-guanidino-pentanoic acid phenethyl-amide dihydrochloride (51 mg, 0.14 mmol) and N-ethylmorpholine (56 μl, 0.42 mmol) in dimethylformamide (10 ml). The mixture was stirred at 22° C. for 15 hours. The solvent was evaporated and the residue was purified by column chromatography (Sephadex LH20, n-butanol/acetic acid/water 17:1:2) to give two stereoisomeric product mixtures. more polar diastereomeric mixture: 41 mg MS m/z 673.6 (M+H)+. less polar diastereomeric mixture: 21 mg MS m/z 673.6 (M+H)+. Total yield: 57%.

Workup

  1. customAt 4° C
  2. customThe solvent was evaporated
  3. customthe residue was purified by column chromatography (Sephadex LH20, n-butanol/acetic acid/water 17:1:2)
  4. customto give two stereoisomeric product mixtures

Sources & evidence

ORD record
ord-fb5cf492de704ecf8a25d38702dae4c7
Source dataset
uspto-grants-2004_07
Patent number
US06759420B1

Reaction notes

Loading…