Benzyl chloroformate → HCID 87671417, compound

HRID 1259298Notes

Reaction equation

HRID 1259298 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][C:13]=1[N:14]([CH3:16])[CH3:15])[C:5]([N:7]([O:9][CH3:10])[CH3:8])=[O:6].C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25]>O1CCCC1.O>[CH3:16][N:14]([CH3:15])[C:13]1[CH:12]=[CH:11][C:4]([C:5](=[O:6])[N:7]([O:9][CH3:10])[CH3:8])=[CH:3][C:2]=1[NH:1][C:24](=[O:25])[O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 3

HCID 10387Benzyl chloroformateHCID 10796Cesium carbonateHCID 61103665HCID 61103665, compound

Product 1

HCID 87671417HCID 87671417, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of EXAMPLE 458B in a mixture of tetrahydrofuran (20 mL) and water (20 mL) was added cesium carbonate (6.02 g, 18.58 mmol) and benzyl chloroformate (1.5 mL, 10.16 mmol). The reaction mixture was stirred at room temperature for 16 hours, and concentrated. The residue was partitioned between ethyl acetate (100 mL) and brine (75 mL). The organic layer was washed with brine, and concentrated. The residual oil was purified by flash chromatography eluting with 40% ethyl acetate in hexanes to provide the title product. MS (DCI/NH3) m/z 358 (M+H)+.

Workup

  1. concentrationconcentrated
  2. customThe residue was partitioned between ethyl acetate (100 mL) and brine (75 mL)
  3. washThe organic layer was washed with brine
  4. concentrationconcentrated
  5. customThe residual oil was purified by flash chromatography
  6. washeluting with 40% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-7a50eaffd87f43839aaf33bfb62c57f3
Source dataset
uspto-grants-2013_06
Patent number
US08466150B2

Reaction notes

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