Ethylmorpholine → HCID 69759352, compound

HRID 1883493Notes

Reaction equation

HRID 1883493 reaction equation
[ClH:1].[Br:2][C:3]1[CH:4]=[C:5]([CH:9]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20](=[NH:22])[NH2:21])=[CH:16][CH:15]=2)[C:10]([OH:12])=O)[CH:6]=[CH:7][CH:8]=1.[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O.C(N1CCOCC1)C.Cl.[NH2:54][C@@H:55]([CH:69]1[CH2:74][CH2:73][CH2:72][CH2:71][CH2:70]1)[C:56]([NH:58][CH2:59][CH:60]1[CH2:65][CH2:64][N:63]([C:66](=[NH:68])[NH2:67])[CH2:62][CH2:61]1)=[O:57]>CN(C)C=O>[ClH:1].[Br:2][C:3]1[CH:4]=[C:5]([CH:9]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20](=[NH:22])[NH2:21])=[CH:16][CH:15]=2)[C:10]([NH:54][C@H:55]([C:56](=[O:57])[NH:58][CH2:59][CH:60]2[CH2:65][CH2:64][N:63]([C:66](=[NH:67])[NH2:68])[CH2:62][CH2:61]2)[CH:69]2[CH2:74][CH2:73][CH2:72][CH2:71][CH2:70]2)=[O:12])[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 7525EthylmorpholineHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 69759112HCID 69759112, compoundHCID 131724495HCID 131724495, compound

Product 1

HCID 69759352HCID 69759352, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To 2-(3-bromo-phenyl)-3-(4-carbamimidoyl-phenyl)-propionic acid hydrochloride (188 mg, 0.49 mmol) in dimethylformamide (30 ml) was added TOTU (164 mg, 0.5 mmol) and N-ethylmorpholine (127 μl, 1 mmol) at 0° C. The mixture was stirred for 30 min at 0° C., 2-amino-N-(1-carbamimidoyl-piperidin-4-ylmethyl)-2-(S)-cyclohexyl-acetamide hydrochloric acid salt (180 mg, 0.49 mmol) was added and the mixture was then allowed to warm to room temperature. After evaporation, the residue was purified by chromotography on Sephadex LH20 employing n-butanol (17): glacial acetic acid (1): water (2) as eluent. Pure fractions were combined. The solvent was evaporated, the residue was taken up in water and hydrochloric acid and lyophilized. Yield: 82 mg of the more polar diastereomer and 71 mg of the less polar diastereomer, MS (FAB) m/z: 624 (M+H)+.

Workup

  1. temperatureto warm to room temperature
  2. customAfter evaporation
  3. customthe residue was purified by chromotography on Sephadex
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-e1821004dbe549b79bf723e9bb3a38c1
Source dataset
uspto-grants-2004_07
Patent number
US06759420B1

Reaction notes

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