4-Methylmorpholine → HCID 86751792, compound

HRID 1941550Notes

Reaction equation

HRID 1941550 reaction equation
Cl.[NH2:2][N:3]=[CH:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:18])[CH2:13][CH2:14][C:15]([OH:17])=O)=[CH:7][CH:6]=1.CN1CCOCC1.ClC(OCC(C)C)=O.Cl.C([O:42][C:43](=[O:51])[CH2:44][C@H:45]([NH2:50])[CH2:46][N:47]=[N+:48]=[N-:49])C1C=CC=CC=1.CN(C1C=CC=CN=1)C>CN(C=O)C>[NH2:2][N:3]=[CH:4][C:5]1[CH:6]=[CH:7][C:8]([NH:11][C:12](=[O:18])[CH2:13][CH2:14][C:15]([NH:50][C@@H:45]([CH2:46][N:47]=[N+:48]=[N-:49])[CH2:44][C:43]([OH:51])=[O:42])=[O:17])=[CH:9][CH:10]=1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 218852-DimethylaminopyridineHCID 62365Isobutyl chloroformateHCID 699519434-[(4-(Aminoiminomethyl)phenyl)amino]-4-oxobutanoic acid hydrochlorideHCID 86751793HCID 86751793, compound

Product 1

HCID 86751792HCID 86751792, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-[[4-(aminoiminomethyl)phenyl]amino]-4-oxobutanoic acid hydrochloride prepared in Example 1, Step 1 (4.6 g, 18.5 mmol) was added to dry DMF (250 ml) followed by N-methylmorpholine (1.8 g, 18.5 mmol) and isobutyl chloroformate (2.8 g, 17 mmol) at 25° C. The mixture was stirred for 5 min. Benzyl-3-amino-4-azido-(3S)-butyrate hydrochloride (1 eq; from Step 1, Example 22) was added followed by dimethylaminopyridine. After 1 h the solvent was removed under reduced pressure and the product purified by reverse phase chromatography (water/acetonitrile) to result in 3.0 g of a white solid. A portion (750 mg) of the benzyl ester was subjected to the saponification conditions as previously described and purified by reverse phase chromatography (water/acetonitrile) to result in 340 mg of a white solid: 1H NMR (d6 -DMSO) δ2.44 (m, 4H), 2.6 (m, 2H), 3.35 (bs, 2H), 4.18 (m, 1H), 7.78 (s, 4H), 8.1 (d, 1H,J=8 Hz), 8.27 (bs, 2H), 9.15 (bs, 2H), 10.40 (s, 1H); MS (FAB) m/z 362.1 (MH+).

Workup

  1. customAfter 1 h the solvent was removed under reduced pressure
  2. customthe product purified by reverse phase chromatography (water/acetonitrile)

Sources & evidence

ORD record
ord-3cf090624823419182e8e15d3fc568f3
Source dataset
uspto-grants-1997_12
Patent number
US05703125

Reaction notes

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