4-Methylmorpholine → HCID 86754472, compound

HRID 618143Notes

Reaction equation

HRID 618143 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=O.[CH2:15]([O:17][C:18](=[O:36])[C@@H:19]([NH:26][S:27]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)(=[O:29])=[O:28])[CH2:20][NH:21][C:22](=[O:25])[CH2:23][NH2:24])[CH3:16].CN1CCOCC1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C=O)C>[CH2:15]([O:17][C:18](=[O:36])[C@@H:19]([NH:26][S:27]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)(=[O:28])=[O:29])[CH2:20][NH:21][C:22](=[O:25])[CH2:23][NH:24][C:12](=[O:14])[CH2:11][CH2:10][CH2:9][CH2:8][NH:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)[CH3:16]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 185181515-[(Pyridin-2-yl)amino]pentanoic acidHCID 86754471HCID 86754471, compound

Product 1

HCID 86754472HCID 86754472, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Acid 3-3 (186 mg, 0.55 mmol), amine 3-6 (150 mg, 0.46 mmol), NMM (0.20 mL, 1.8 mmol) and BOP (302 mg, 0.68 mmol) were combined in 3 mL DMF. After 5 d the DMF was removed on a rotary evaporator, the residue was diluted with EtOAc, then washed with water, sat. NaHCO3, and brine, dried (MgSO4), filtered and concentrated. Flash chromatography (silica, 25% i-PrOH/EtOAc) provided 3-7 as a colorless oil.

Workup

  1. customAfter 5 d the DMF was removed on a rotary evaporator
  2. additionthe residue was diluted with EtOAc
  3. washwashed with water, sat. NaHCO3, and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-13a41fdd8eaf4fbc896b67b69da2549d
Source dataset
uspto-grants-1999_09
Patent number
US05952306

Reaction notes

Loading…