Ethylmorpholine → HCID 178476625, compound

HRID 1883487Notes

Reaction equation

HRID 1883487 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH:11]([CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)[C:12]([N:14]([CH2:22][C:23]([OH:25])=[O:24])[CH2:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[O:13])=[CH:6][CH:5]=1)(=[NH:3])[NH2:2].[ClH:32].Cl.[NH2:34][C@@H:35]([CH2:39][CH2:40][CH2:41][NH:42][C:43]([NH2:45])=[NH:44])[C:36]([NH2:38])=[O:37].[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O.C(N1CCOCC1)C>CN(C)C=O>[ClH:32].[C:23]([OH:25])(=[O:24])[CH3:22].[C:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH:11]([CH:26]2[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]2)[C:12]([N:14]([CH2:15][CH:16]2[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]2)[CH2:22][C:23]([NH:34][C@@H:35]([CH2:39][CH2:40][CH2:41][NH:42][C:43]([NH2:45])=[NH:44])[C:36]([NH2:38])=[O:37])=[O:24])=[O:13])=[CH:8][CH:9]=1)(=[NH:3])[NH2:2]

Participants

6

Reactant 4

HCID 7525EthylmorpholineHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 23509940HCID 23509940, compoundHCID 178478814HCID 178478814, compound

Product 1

HCID 178476625HCID 178476625, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To {[3-(4-carbamimidoyl-phenyl)-2-2-(R,S)-cyclohexyl-propionyl]-cyclohexylmethyl-amino}-acetic acid (50 mg, 0.12 mmol) and 2-(S)-amino-5-guanidino-pentanoic acid amide dihyrochloride (30 mg, 0.12 mmol) in dimethylformamide (5 ml) were added at −15° C. TOTU (44 mg, 0.13 mmol) and N-ethylmorpholine (40 μl, 0.32 mmol). The mixture was stirred for 1 hour and then allowed to warm to room temperature. After evaporated, the residue was treated with sodium bicarbonate solution and extracted with ethyl acetate. The aqueous layer was evaporated and purified by chromatography 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 the aqueous solution was lyophilized. Yield: 12 mg (15%), MS m/z: 292.4 (M+2H)2+.

Workup

  1. customAfter evaporated
  2. additionthe residue was treated with sodium bicarbonate solution
  3. extractionextracted with ethyl acetate
  4. customThe aqueous layer was evaporated
  5. custompurified by chromatography on Sephadex
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-b2d4d1b4b5cd42c3bce8040477a46af9
Source dataset
uspto-grants-2004_07
Patent number
US06759420B1

Reaction notes

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