Water → HCID 131734212, compound

HRID 1497534Notes

Reaction equation

HRID 1497534 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12](NC(=O)OC(C)(C)C)=[C:11]([Cl:23])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].IC.[OH2:28].C[N:30]([CH3:33])[CH:31]=[O:32]>>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:33][NH:30][C:31](=[O:28])[O:32][C:2]([CH3:7])([CH3:3])[CH3:1])=[C:11]([Cl:23])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 131734213HCID 131734213, compound

Product 1

HCID 131734212HCID 131734212, compound

Procedure

To a solution of tert-butyl [4-(benzyloxy)-2-chlorophenyl]carbamate (3.00 g) in N,N-dimethylformamide (45.0 mL) was added 55% sodium hydride (471 mg) under ice-cooling and a nitrogen flow, followed by stirring for 30 minutes under ice-cooling. Iodomethane (0.673 mL) was added thereto under ice-cooling, followed by stirring for 30 minutes. To the reaction mixture was added water, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain tert-butyl [4-(benzyloxy)-2-chlorophenyl]methylcarbamate (1.42 g).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. temperatureunder ice-cooling
  4. stirringby stirring for 30 minutes
  5. extractionfollowed by extraction with ethyl acetate
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-89e360bd6f98416cbbc79a90aca62b62
Source dataset
uspto-grants-2015_12
Patent number
US09199927B2

Reaction notes

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