Trifluoroacetic acid methylene chloride → (7-Methanesulfonylamino-1,1-dioxo-1,4-dihydro-1lambda6-benzo[1,4]thiazin-3-yl)-acetic acid ethyl ester

HRID 731310Notes

Reaction equation

HRID 731310 reaction equation
[CH2:1]([O:3][C:4](=[O:37])[CH2:5][C:6]1[N:11](C(OC(C)(C)C)=O)[C:10]2[CH:19]=[CH:20][C:21]([N:23]([S:31]([CH3:34])(=[O:33])=[O:32])C(OC(C)(C)C)=O)=[CH:22][C:9]=2[S:8](=[O:36])(=[O:35])[CH:7]=1)[CH3:2].ClCCl.FC(F)(F)C(O)=O>>[CH2:1]([O:3][C:4](=[O:37])[CH2:5][C:6]1[NH:11][C:10]2[CH:19]=[CH:20][C:21]([NH:23][S:31]([CH3:34])(=[O:33])=[O:32])=[CH:22][C:9]=2[S:8](=[O:36])(=[O:35])[CH:7]=1)[CH3:2]

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 59853597[7-(Methanesulfonyl-tert-butyloxycarbonyl-amino)-4-tert-butyloxycarbonyl-1,1-dioxo-1,4-dihydro-1lambda6-benzo[1,4]thiazin-3-yl]-acetic acid ethyl ester

Product 1

HCID 59853588(7-Methanesulfonylamino-1,1-dioxo-1,4-dihydro-1lambda6-benzo[1,4]thiazin-3-yl)-acetic acid ethyl esterYield 87%

Procedure

A solution of [7-(methanesulfonyl-tert-butyloxycarbonyl-amino)-4-tert-butyloxycarbonyl-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,4]thiazin-3-yl]-acetic acid ethyl ester (0.30 g, 0.54 mmol) in 1:1 dichloromethane/trifluoroacetic acid was stirred at 25° C. for 2 h. The reaction mixture was concentrated in vacuo and the residue was dissolved in ethyl acetate. The solution was washed with saturated aqueous sodium bicarbonate solution and saturated aqueous brine solution. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo to afford the desired product, (7-methanesulfonylamino-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,4]thiazin-3-yl)-acetic acid ethyl ester (0.17 g, 0.47 mmol, 86%) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ 1.32 (t, 3H, J=6.9 Hz), 3.03 (s, 3H), 4.02 (s, 2H), 4.21 (q, 2H, J=7.0 Hz), 5.02 (s, 1H), 6.96 (s, 1H), 7.02 (d, 1H, J=8.4 Hz), 7.53 (dd, 1H, J1=8.7 Hz, J2=2.4 Hz), 7.65 (d, 1H, J=2.2 Hz), 10.73 (s, 1H). LC-MS (ESI) calcd for C13H16N2O6S2 [M+H+] 361.04, found 361.18 [M+H+].

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washThe solution was washed with saturated aqueous sodium bicarbonate solution and saturated aqueous brine solution
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-962a3b6e62924c88a85f33840a34559c
Source dataset
uspto-grants-2009_09
Patent number
US07582626B2

Reaction notes

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