Hydrochloric Acid → HCID 76578003, compound

HRID 2197266Notes

Reaction equation

HRID 2197266 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][O:15][CH2:16][CH:17]3[C:21](=[O:22])[N:20]([CH:23]([CH:27]([CH3:29])[CH3:28])[C:24](O)=[O:25])[C:19](=[O:30])[NH:18]3)=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.CN([P+]([O:41][N:42]1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.ON.Cl.CN1CCOCC1>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[CH:10][C:11]([CH2:14][O:15][CH2:16][CH:17]3[C:21](=[O:22])[N:20]([CH:23]([CH:27]([CH3:28])[CH3:29])[C:24]([NH:42][OH:41])=[O:25])[C:19](=[O:30])[NH:18]3)=[CH:12][CH:13]=2)[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 787HydroxylamineHCID 79724-MethylmorpholineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 76578007HCID 76578007, compound2×

Product 1

HCID 76578003HCID 76578003, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the compound obtained in step c above (20c) (166 mg, 0.401 mmol) in DMF (5 mL) was added BOP reagent (213 mg, 0.481 mmol) at 0° C. After stirring for 30 min, HONH2×HCl (50 mg, 11.38 mmol) and N-methylmorpholine (0.15 mL, 1.34 mmol) were added. The mixture was warmed to room temperature and stirred overnight. The solvent was removed and the residue was partitioned between EtOAc and saturated NH4Cl solution. The aqueous layer was extracted with EtOAc, the organic layer was dried and concentrated. The residue was purified by silica gel column chromatography to afford the title compound as a white solid (60 mg, 35%).

Workup

  1. stirringstirred overnight
  2. customThe solvent was removed
  3. customthe residue was partitioned between EtOAc and saturated NH4Cl solution
  4. extractionThe aqueous layer was extracted with EtOAc
  5. customthe organic layer was dried
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c539219c0d6d4ceca2f388faa10161e0
Source dataset
uspto-grants-2012_12
Patent number
US08338471B2

Reaction notes

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