Hydrochloric Acid → HCID 16718426, compound

HRID 2197261Notes

Reaction equation

HRID 2197261 reaction equation
[O:1]=[C:2]1[NH:6][CH:5]([CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:4](=[O:15])[N:3]1[CH:16]([CH:20]([CH3:22])[CH3:21])[C:17](O)=[O:18].F[P-](F)(F)(F)(F)F.[N:30]1([O:39][P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.ON.Cl.CN1CCOCC1>CN(C=O)C>[O:1]=[C:2]1[NH:6][CH:5]([CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:4](=[O:15])[N:3]1[CH:16]([CH:20]([CH3:22])[CH3:21])[C:17]([NH:30][OH:39])=[O:18]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 787HydroxylamineHCID 79724-MethylmorpholineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 76578026HCID 76578026, compound

Product 1

HCID 16718426HCID 16718426, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the compound obtained in step e above (109 mg, 0.36 mmol) in DMF (1.8 mL) was added BOP (190 mg, 0.43 mmol) at 0° C. After stirring for 30 min, HONH2×HCl (50 mg, 11.38 mmol) and N-methylmorpholine (0.16 mL, 1.44 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 a saturated solution of NH4Cl. The aqueous layer was extracted with EtOAc, dried and concentrated. The residue was purified by silica gel column chromatography to afford the title compound as a white solid (63 mg, 55% yield).

Workup

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

Sources & evidence

ORD record
ord-3b85c07236e84d188f167368b4216c98
Source dataset
uspto-grants-2012_12
Patent number
US08338471B2

Reaction notes

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