4-Methylmorpholine → 3(S)-(Pyridin-3-yl)-3-(5-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-pentanoylamino)propionic acid ethyl ester

HRID 1837871Notes

Reaction equation

HRID 1837871 reaction equation
Cl.[N:2]1[C:11]2[NH:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:5]=[CH:4][C:3]=1[CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=O.F[P-](F)(F)(F)(F)F.[N:26]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34]C=2N=N1.[CH3:46][N:47]1CCOCC1.[C:53]([O:56][CH2:57][CH3:58])(=[O:55])[CH3:54]>CC#N>[CH2:57]([O:56][C:53](=[O:55])[CH2:54][C@@H:46]([C:33]1[CH:34]=[N:26][CH:30]=[CH:31][CH:32]=1)[NH:47][C:16](=[O:18])[CH2:15][CH2:14][CH2:13][CH2:12][C:3]1[CH:4]=[CH:5][C:6]2[CH2:7][CH2:8][CH2:9][NH:10][C:11]=2[N:2]=1)[CH3:58]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 8857Ethyl AcetateHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 697750595-(5,6,7,8-Tetrahydro-1,8-naphthyridin-2-yl)pentanoic acid hydrochloride

Product 1

HCID 544418963(S)-(Pyridin-3-yl)-3-(5-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-pentanoylamino)propionic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-6 (50 mg, 0.1847 mmol), 1-7 (49 mg, 0.1847 mmol) (Rico et al., J. Org. Chem., 1993, 58, 7948), BOP (90 mg, 0.2032 mmol) and NMM (0.122 mL, 1.11 mmol) in CH3CN (2 mL) was stirred for 18 h. The mixture was diluted with ethyl acetate, washed with sat. NaHCO3, brine, and dried over MgSO4. Following evaporative removal of the solvent, the residue was chromatographed (silica gel, 20% MeOH/ethyl acetate) to give 1-8 as a yellow oil.

Workup

  1. washwashed with sat. NaHCO3, brine
  2. dry with materialdried over MgSO4
  3. customremoval of the solvent
  4. customthe residue was chromatographed (silica gel, 20% MeOH/ethyl acetate)

Sources & evidence

ORD record
ord-4a00a012af9d4e899a9273bf8579ed89
Source dataset
uspto-grants-2004_08
Patent number
US06784190B2

Reaction notes

Loading…