Water → Benzyl carbamate

HRID 2281978Notes

Reaction equation

HRID 2281978 reaction equation
O.NN.[N:4]1C=CC=CC=1.Cl[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12].O>O1CCCC1.C(OCC)(=O)C>[C:11](=[O:12])([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[NH2:4]

Participants

7

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 10387Benzyl chloroformateHCID 24654Hydrazine hydrate (1:1)

Product 1

HCID 12136Benzyl carbamate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

The compound obtained in Example 190, (1) (200 mg) was dissolved in tetrahydrofuran (2 ml), pyridine (58 μl) and benzyl chloroformate (68 μl) were added to the solution, and the resulting mixture was stirred at room temperature for 10 minutes. Distilled water and ethyl acetate were added to the reaction mixture, and the layers were separated. The organic layer was washed with saturated aqueous sodium chloride, then dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (ethyl acetate:methanol:28% aqueous ammonia=8:1:0.1) to obtain a benzyl carbamate compound (191 mg). (2) By using the compound obtained in (1) mentioned above (186 mg) as a starting material, a deprotected compound (156 mg) was obtained in the same manner as that of Example 4, (6). (3) By using the compound obtained in (2) mentioned above (60 mg) as a starting material, the compound shown in Table 5 (65 mg) was obtained in the same manner as that of Example 11.

Workup

  1. customthe layers were separated
  2. washThe organic layer was washed with saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe resulting residue was purified by silica gel column chromatography (ethyl acetate:methanol:28% aqueous ammonia=8:1:0.1)

Sources & evidence

ORD record
ord-6c64e936d1de47dc855d24dc1f5f8064
Source dataset
uspto-grants-2015_09
Patent number
US09139609B2

Reaction notes

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