Trifluoroacetic acid → HCID 23660310, compound

HRID 1435455Notes

Reaction equation

HRID 1435455 reaction equation
[C:1]([C:5]1[N:9]([CH2:10][CH:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[C:8]2[CH:17]=[CH:18][C:19]([S:21]([N:24]3[CH2:27][CH:26]([NH:28]C(=O)OC(C)(C)C)[CH2:25]3)(=[O:23])=[O:22])=[CH:20][C:7]=2[N:6]=1)([CH3:4])([CH3:3])[CH3:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:1]([C:5]1[N:9]([CH2:10][CH:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[C:8]2[CH:17]=[CH:18][C:19]([S:21]([N:24]3[CH2:25][CH:26]([NH2:28])[CH2:27]3)(=[O:23])=[O:22])=[CH:20][C:7]=2[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57937324HCID 57937324, compound

Product 1

HCID 23660310HCID 23660310, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-butyl (1-{[2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]sulfonyl}azetidin-3-yl)carbamate (0.84 g, 1.66 mmol) (see following step B for preparation) in CH2Cl2 (10 mL) was treated with TFA (5 mL) for 1 h at room temperature. Upon evaporation, the residue was dissolved in H2O (20 mL), neutralized with 2 N NaOH to pH=10, and extracted with CH2Cl2 (5×30 mL). The combined organic phases were washed with NaCl (10 mL) and dried over Na2SO4. After concentration, 0.58 g (86%) of a white solid was obtained as the title compound. 1H NMR (400 MHz, METHANOL-D4) δ 1.45-1.62 (m, 4 H), 1.63 (s, 9 H), 2.28-2.44 (m, 1 H), 3.30-3.39 (m, 2 H), 3.82-3.89 (m, 3 H), 3.89-3.97 (m, 2 H), 3.99-4.10 (m, 2 H), 4.48 (d, J=7.62 Hz, 2 H), 7.85 (dd, J=8.69, 1.66 Hz, 1 H), 7.98 (d, J=8.79 Hz, 1 H), 8.15 (d, J=1.76 Hz, 1 H); MS (ESI) (M+H)+=407.0; Anal. Calcd for C20H30N4O3S+2.10 TFA+0.20 CH3OH+0.20H2O (656.01): C, 44.67; H, 5.12; N, 8.54. Found: C, 44.68; H, 5.15; N, 8.56.

Workup

  1. customUpon evaporation
  2. dissolutionthe residue was dissolved in H2O (20 mL)
  3. extractionextracted with CH2Cl2 (5×30 mL)
  4. washThe combined organic phases were washed with NaCl (10 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationAfter concentration

Sources & evidence

ORD record
ord-abf29513220343c0a98a3106e353068e
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

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