Water → HCID 66661034, compound

HRID 910407Notes

Reaction equation

HRID 910407 reaction equation
[CH3:1][O:2][C:3](=[O:21])[CH:4]([NH:8][C:9](=[O:20])[CH:10]([NH2:19])[CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH:5]([CH3:7])[CH3:6].O.Cl[C:24]([O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:25].CCN(C(C)C)C(C)C>O1CCOCC1>[CH3:1][O:2][C:3](=[O:21])[CH:4]([NH:8][C:9](=[O:20])[CH:10]([NH:19][C:24]([O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:25])[CH2:11][CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[CH:5]([CH3:6])[CH3:7]

Participants

6

Reactant 4

HCID 962WaterHCID 15891Phenyl chloroformateHCID 81531DiisopropylethylamineHCID 66661062HCID 66661062, compound

Product 1

HCID 66661034HCID 66661034, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a mixture of the crude compound obtained in step b above (1400 mg) in dioxane (18 mL) and water (2 mL) was added phenyl chloroformate (0.9 mL, 7.16 mmol) and DIEA (1.6 mL, 8.95 mmol). The mixture was stirred at room temperature for 3 h and concentrated under reduced pressure. The residue was partitioned between water and EtOAc. The aqueous layer was extracted with EtOAc, the combined organic phases were dried and concentrated. The residue was purified by silica gel column chromatography to afford the title compound as a white solid (1165 mg, 79% yield, three steps).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was partitioned between water and EtOAc
  3. extractionThe aqueous layer was extracted with EtOAc
  4. customthe combined organic phases were dried
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4b911612e5cb4024976a1abb65264d55
Source dataset
uspto-grants-2011_09
Patent number
US08022092B2

Reaction notes

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