Benzyl chloroformate → HCID 22291160, compound

HRID 1582424Notes

Reaction equation

HRID 1582424 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[CH:9]1[CH2:15][NH:14][CH2:13][CH2:12][CH2:11][N:10]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[NH2:5].C(=O)(O)[O-].[Na+].[CH2:28]([O:35][C:36](Cl)=[O:37])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C1COCC1>[CH2:28]([O:35][C:36]([NH:5][C:4]1[CH:6]=[CH:7][C:8]([CH:9]2[CH2:15][NH:14][CH2:13][CH2:12][CH2:11][N:10]2[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[C:2]([F:1])[CH:3]=1)=[O:37])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 69352853HCID 69352853, compound

Product 1

HCID 22291160HCID 22291160, compoundYield 135.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 3-Fluoro-4-(N-tert-butoxycarbonylhomopiperazinyl)aniline (2.6 g, 8.4 mmol) in THF (25 ml) cooled to 5° C., sodium bicarbonate (0.85 g 10.1 mmol), was added and then benzylchloroformate (1.72 g, 10 mmol) was added dropwise. The reaction mixture was stirred for 18 hrs. at R.T. and then filtered. The filtrate was evaporated in vacuo. The residue was dissolved in dichloromethane and washed with saturated sodium bicarbonate solution and brine water. The organic layer was dried over anhyd Na2SO4 and evaporated in vacuo to give 5.04 g of final product.

Workup

  1. filtrationat R.T. and then filtered
  2. customThe filtrate was evaporated in vacuo
  3. dissolutionThe residue was dissolved in dichloromethane
  4. washwashed with saturated sodium bicarbonate solution and brine water
  5. dry with materialThe organic layer was dried over anhyd Na2SO4
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-d16c5f698a824e3cb83e3572a1187d7f
Source dataset
uspto-grants-2004_05
Patent number
US06734307B2

Reaction notes

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