Trifluoroacetic acid → HCID 66864756, compound

HRID 1192912Notes

Reaction equation

HRID 1192912 reaction equation
[CH2:1]([O:3][C:4](=[O:32])[CH2:5][C:6]1([NH:17][S:18]([C:21]2[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[CH:23][CH:22]=2)(=[O:20])=[O:19])[CH2:9][N:8](C(OC(C)(C)C)=O)[CH2:7]1)[CH3:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:27]([C:24]1[CH:23]=[CH:22][C:21]([S:18]([NH:17][C:6]2([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:32])[CH2:9][NH:8][CH2:7]2)(=[O:20])=[O:19])=[CH:26][CH:25]=1)[CH2:28][CH2:29][CH2:30][CH3:31]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86649848tert-Butyl 3-(2-ethoxy-2-oxoethyl)-3-(4-pentylphenylsulfonamido)azetidine-1-carboxylate

Product 1

HCID 66864756HCID 66864756, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 3-(2-ethoxy-2-oxoethyl)-3-(4-pentylphenylsulfonamido)azetidine-1-carboxylate (79 mg, 0.169 mmol) was dissolved into DCM (4 mL). The solution was treated with TFA (0.3 mL). The mixture was stirred at room temperature for 4 h. DCM was removed under vacuum. Ethyl acetate (25 mL) was added and the solution was washed with saturated sodium bicarbonate (2×5 mL), water (10 mL), brine (10 mL), dried over MgSO4 and concentrated to afford the title compound as a white powder (52 mg, 84%). 1H NMR (400 MHz, CDCl3) δ 7.79 (d, 2H, J=8 Hz), 7.31 (d, 2H, J=8 Hz), 4.05 (q, 2H, J=7.2 Hz), 3.94 (d, 2H, J=8.8 Hz), 3.36 (d, 2H, J=8.8 Hz), 3.01 (s, 2H), 2.68 (t, 2H, J=8 Hz), 1.66 (m, 2H), 1.34 (br, 4H), 1.22 (t, 3H, J=7.2 Hz), 0.90 (t, 3H, J=6.8 Hz); MS ESI 369.1 [M+H]+, calcd for [C18H28N2O4S+H]+ 369.18.

Workup

  1. customDCM was removed under vacuum
  2. additionEthyl acetate (25 mL) was added
  3. washthe solution was washed with saturated sodium bicarbonate (2×5 mL), water (10 mL), brine (10 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-19dfe5320e164fe2b6f5de917f1a1a28
Source dataset
uspto-grants-2014_03
Patent number
US08680282B2

Reaction notes

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