2,6-Lutidine → HCID 21887970, compound

HRID 863244Notes

Reaction equation

HRID 863244 reaction equation
FC(F)(F)S(O[Si](C)(C)C)(=O)=O.C(OC([N:20]1[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[CH2:23][S:22][CH2:21]1)=O)(C)(C)C.N1C(C)=CC=CC=1C>C(Cl)Cl.CO>[NH:20]1[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[CH2:23][S:22][CH2:21]1

Participants

6

Reactant 3

HCID 79372,6-LutidineHCID 65367Trimethylsilyl triflateHCID 19697752HCID 19697752, compound

Product 1

HCID 21887970HCID 21887970, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

1.47 ml of trimethylsilyl trifluoromethanesulfonate are added dropwise to a solution of 1.0 g of N-tert-butoxycarbonyl-3,4-dihydro-1H-2,4-benzothiazine in 35 ml of methylene chloride at room temperature, and 1.41 ml of 2,6-lutidine is added. The reaction mixture is stirred at room temperature for 20 minutes and then diluted with 5 ml of methanol and concentrated. The crude product is purified by means of FC (30 g of silica gel, mobile phase G). This gives the pure title compound: Rf (D)=0.26; Rt (I)=19.5 min; anal. calc. for C8H9NS: C 63.54%, H 6.00%, N 9.26%; found C 63.22%. H 6.01%, N 8.99%.

Workup

  1. concentrationconcentrated
  2. customThe crude product is purified by means of FC (30 g of silica gel, mobile phase G)

Sources & evidence

ORD record
ord-bb502f0755194863b70cb98603cdab7b
Source dataset
uspto-grants-1998_02
Patent number
US05719141

Reaction notes

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