4-Methylmorpholine → HCID 86752454, compound

HRID 583696Notes

Reaction equation

HRID 583696 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[NH:7][CH2:8][CH2:9][O:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=O)=[CH:13][CH:12]=1.Cl.C(OC(N[C@@H:32]([CH2:40][NH2:41])[C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])=O)C1C=CC=CC=1.C[N:43]1CCOCC1.CN([P+](ON1N=N[C:62]2[CH:63]=[CH:64][CH:65]=[CH:66][C:61]1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.C[CH2:77][O:78][C:79](C)=[O:80]>CN(C=O)C>[C:36]([O:35][C:33](=[O:34])[C@H:32]([C:79]([O:78][CH2:77][C:61]1[CH:62]=[CH:63][CH:64]=[CH:65][CH:66]=1)=[O:80])[CH2:40][N:41]([C:15](=[O:17])[C:14]1[CH:13]=[CH:12][C:11]([O:10][CH2:9][CH2:8][NH:7][C:2]2[N:1]=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:19][CH:18]=1)[NH2:43])([CH3:37])([CH3:38])[CH3:39]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 8857Ethyl AcetateHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 10777662Benzoic acid, 4-[2-(2-pyrimidinylamino)ethoxy]-HCID 22885054tert-Butyl 2(S)-Benzyloxycarbonylamino-3-aminopropionate hydrochloride

Product 1

HCID 86752454HCID 86752454, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 19-6 (400 mg, 1.5 mmol), 25-a (538, 1.6 mmol), DMF (10 mL), and NMM (6.27 mg, 6.0 mmol) at ambient temperature was added BOP reagent (717 mg, 1.6 mmol). After 24 h, the reaction mixture was diluted with EtOAc and then washed with H2O and brine, dried (MgSO4) and concentrated. Flash chromatograpy (silica, 60% EtOAc/hexanes) gave 25-1 as a yellow oil. TLC Rf 0.14 (silica, 60% EtOAc/hexanes);

Workup

  1. washwashed with H2O and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-a197989be96e48f5bcdce420eaf1bcda
Source dataset
uspto-grants-1999_07
Patent number
US05929120

Reaction notes

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