Benzyl chloroformate → Phenylmethyl [3-fluoro-4-[tetrahydro-1,1-dioxido-2-(2-propenyl)-2H-1,2-thiazin-4-yl]phenyl]carbamate

HRID 2229139Notes

Reaction equation

HRID 2229139 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH2:19])[CH:5]=[CH:6][C:7]=1[CH:8]1[CH2:13][CH2:12][S:11](=[O:15])(=[O:14])[N:10]([CH2:16][CH:17]=[CH2:18])[CH2:9]1.Cl[C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22].C(=O)(O)[O-].[Na+]>C1COCC1.O>[F:1][C:2]1[CH:3]=[C:4]([NH:19][C:21](=[O:22])[O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:5]=[CH:6][C:7]=1[CH:8]1[CH2:13][CH2:12][S:11](=[O:15])(=[O:14])[N:10]([CH2:16][CH:17]=[CH2:18])[CH2:9]1

Participants

6

Reactant 3

HCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 220912753-fluoro-4-[tetrahydro-1,1-dioxido-2-(2-propenyl)-2H-1,2-thiazin-4-yl]benzenamine

Product 1

HCID 12019397Phenylmethyl [3-fluoro-4-[tetrahydro-1,1-dioxido-2-(2-propenyl)-2H-1,2-thiazin-4-yl]phenyl]carbamateYield 100.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

3-fluoro-4-[tetrahydro-1,1-dioxido-2-(2-propenyl)-2H-1,2-thiazin-4-yl]benzenamine (1.154 g, 4.06 mmol) is dissolved in THF (15 ml) to which is added benzyl chloroformate (765 mg, 4.48 mmol) followed by a solution of sodium bicarbonate (700 mg, 8.33 mmol) in water (10 ml). After stirring for 2 hr most of the THF is evaporated and the residue is extracted with ethyl acetate (100 ml). After washing with water (25 ml) and brine, the solution is dried (MgSO4) and evaporated to afford the title compound as white crystals (1.70 g, 100%) mp 138-140°.

Workup

  1. customis evaporated
  2. extractionthe residue is extracted with ethyl acetate (100 ml)
  3. washAfter washing with water (25 ml) and brine
  4. dry with materialthe solution is dried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-60ac9315d3964f22b863d6dfc604489a
Source dataset
uspto-grants-2002_07
Patent number
US06420360B1

Reaction notes

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