(Diethylamino)sulfur trifluoride → HCID 22916662, compound

HRID 1376613Notes

Reaction equation

HRID 1376613 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[S:11][CH:12]=[C:13]([CH2:15]O)[N:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(S(F)(F)[F:23])CC)C.C(=O)([O-])O.[Na+]>ClCCl>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[S:11][CH:12]=[C:13]([CH2:15][F:23])[N:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 22916663165667-51-6

Product 1

HCID 22916662HCID 22916662, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.0 g of the above-obtained 2-(tert-butoxycarbonylamino)methyl-4-hydroxymethylthiazole in 20 ml of dichloromethane was added 0.6 ml of diethylaminosulphur trifluoride with ice-cooling, and the mixture was stirred at room temperature for 30 minutes. To this reaction solution was added 20 ml of a saturated aqueous solution of sodium hydrogencarbonate, and the mixture was stirred for 10 minutes. The organic layer was separated, and the aqueous layer was extracted with dichloromethane (10 ml×2). The combined organic layers were dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography, eluting with a 50:1 mixture of chloroform and methanol to give 0.535 g (yield 47%) of the title compound.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 10 minutes
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with dichloromethane (10 ml×2)
  5. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography
  8. washeluting with a 50:1 mixture of chloroform and methanol

Sources & evidence

ORD record
ord-b9b5ea9df658433ba756e1e123bf7a9c
Source dataset
uspto-grants-1997_09
Patent number
US05663162

Reaction notes

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