Ethylmorpholine → HCID 131723237, compound

HRID 1937824Notes

Reaction equation

HRID 1937824 reaction equation
C(N1CCOCC1)C.[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O.Cl.[CH2:32]([NH:39][C:40]([CH:42]([CH2:56][C:57]1[CH:62]=[CH:61][C:60]([C:63](=[NH:65])[NH2:64])=[CH:59][CH:58]=1)[C:43]([NH:45][C@@H:46]([CH:50]1[CH2:55][CH2:54][CH2:53][CH2:52][CH2:51]1)[C:47](O)=[O:48])=[O:44])=[O:41])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.[C:66]([O:70][C:71]([N:73]1[CH2:78][CH2:77][N:76]([CH2:79][CH2:80][NH2:81])[CH2:75][CH2:74]1)=[O:72])([CH3:69])([CH3:68])[CH3:67]>CN(C)C=O>[C:66]([O:70][C:71]([N:73]1[CH2:74][CH2:75][N:76]([CH2:79][CH2:80][NH:81][C:47](=[O:48])[C@@H:46]([NH:45][C:43](=[O:44])[CH:42]([C:40](=[O:41])[NH:39][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:56][C:57]2[CH:58]=[CH:59][C:60]([C:63](=[NH:65])[NH2:64])=[CH:61][CH:62]=2)[CH:50]2[CH2:55][CH2:54][CH2:53][CH2:52][CH2:51]2)[CH2:77][CH2:78]1)=[O:72])([CH3:69])([CH3:68])[CH3:67]

Participants

6

Reactant 4

HCID 7525EthylmorpholineHCID 1514400tert-Butyl 4-(2-aminoethyl)piperazine-1-carboxylateHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 131723238HCID 131723238, compound

Product 1

HCID 131723237HCID 131723237, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

N-ethyl-morpholine (28 μl, 0.22 mmol) and TOTU (78 mg, 0.24 mmol) was added to a solution of [2-benzylcarbamoyl-3-(4-carbamimidoyl-phenyl)-propionylamino]-(S)-cyclohexyl-acetic acid hydrochloric acid salt, (100 mg, 0.2 mmol, example 3 h, less polar diastereomer) in dimethylformamide (4 ml) at −15 to −20° C. After 30 min at that temperature 4-(2-amino-ethyl)-piperazine-1-carboxylic acid tert-butyl ester (55 mg, 0.24 mmol, step a) in dimethylformamide (1 ml) was added and stirred for 2 more hours. The reaction mixture was warmed to room temperature and stand over night. The solvent was evaporated in vacuo, stirred for 2 days with diethyl ether, and the precipitate collected by suction to give the title compound in quantitative yield. mp.: 125-128° C., MS m/z: 676 ((M+H)+, 3%), 339.0 ((M+2H)2+, 100%).

Workup

  1. custom100 mg, 0.2 mmol, example 3 h, less polar diastereomer
  2. customat −15 to −20° C
  3. waitstand over night
  4. customThe solvent was evaporated in vacuo
  5. stirringstirred for 2 days with diethyl ether
  6. customthe precipitate collected by suction

Sources & evidence

ORD record
ord-d291572689364d6fa099207dcbebe2b2
Source dataset
uspto-grants-2002_05
Patent number
US06395737B1

Reaction notes

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