4-Methylmorpholine → HCID 67601154, compound

HRID 618144Notes

Reaction equation

HRID 618144 reaction equation
[C:1]([C:8]1[C:13]([NH2:14])=[C:12]([CH2:15][CH2:16][CH2:17][C:18]([N:20]([CH2:22][C:23]([OH:25])=[O:24])[CH3:21])=[O:19])[CH:11]=[CH:10][N:9]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CN1CCOCC1.F[P-](F)(F)(F)(F)F.[N:40]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][C:43]=2N=N1>CC#N.CCOC(C)=O>[C:1]([C:8]1[C:13]([NH2:14])=[C:12]([CH2:15][CH2:16][CH2:17][C:18]([N:20]([CH2:22][C:23]([OH:25])=[O:24])[CH3:21])=[O:19])[CH:11]=[CH:10][N:9]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH2:4]([O:3][C:1](=[O:2])[CH2:8][C@@H:13]([CH2:12][CH2:15][C:16]1[C:43]2[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=2)[NH:40][CH:17]=1)[NH2:14])[CH3:5]

Participants

6

Reactant 3

HCID 79724-MethylmorpholineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 67601156HCID 67601156, compound

Product 1

HCID 67601154HCID 67601154, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

Acid 4-3 (84 mg, 0.24 mmol), amine 4-4 (see Duggan et al., U.S. Pat. No. 5,264,420) (68 mg, 0.26 mmol), NMM (104 μL, 0.95 mmol) and BOP (127 mg, 0.29 mmol) were combined in 2.4 mL CH3CN. After stirring overnight the mixture was diluted with EtOAc, washed with water (4×), sat. NaHCO3, and brine, dried (MgSO4) and concentrated. Flash chromatography (silica, EtOAc) provided 4-5 as a colorless oil

Workup

  1. washwashed with water (4×), sat. NaHCO3, and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-c4f1edd56c7e4cef996c6cacfa0c3b49
Source dataset
uspto-grants-1999_09
Patent number
US05952306

Reaction notes

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