4-Methylmorpholine → HCID 86752454, compound

HRID 1599944Notes

Reaction equation

HRID 1599944 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.

Workup

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

Sources & evidence

ORD record
ord-303dc44cb3b142919230261a93694faa
Source dataset
uspto-grants-1998_04
Patent number
US05741796

Reaction notes

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