HCID 91028084, compound → HCID 69314944, compound

HRID 2389486Notes

Reaction equation

HRID 2389486 reaction equation
C([O:5][C:6](=[O:37])[CH2:7][N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[S:17][CH2:18][CH2:19][CH2:20][N:21]([C:30]([O:32][CH2:33][CH2:34][CH2:35][CH3:36])=[O:31])[CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(C)(C)C>C(O)(C(F)(F)F)=O.ClCCl>[CH2:33]([O:32][C:30]([N:21]([CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:20][CH2:19][CH2:18][S:17][C:9]1[N:8]([CH2:7][C:6]([OH:37])=[O:5])[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=1)=[O:31])[CH2:34][CH2:35][CH3:36]

Participants

3

Reactant 1

HCID 91028084HCID 91028084, compound

Product 1

HCID 69314944HCID 69314944, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of tert-butyl{2-[3-(butoxycarbonyl-phenethyl-amino)-propylsulfanyl]-benzoimidazol-1-yl}-acetate (Precursor K-01b, 200 mg, 0.38 mmol) is dissolved in TFA/dichloromethane (1:1, 3 ml). The resulting solution is allowed to stir at rt overnight. The solvent is evaporated under reduced pressure and the crude product is triturated in Et2O (2 ml) until a solid forms. It is filtered, washed thoroughly with Et2O and dried under high vacuum, yielding quantitatively the title compound (179 mg) as a white powder: tR=6.82 min (LC-1), ESI-MS (neg.): m/z 470.19 [M−H]+, ESI-MS (neg.): m/z 468.32 [M−H]+; 1H-NMR (CDCl3): δ (ppm) 0.82 (t, 3H, CH2CH3), 1.29 (m, 2H, CH2CH3), 1.48 (quint., 2H, OCH2CH2), 1.71 (m; 2H, SCH2CH2), 2.67 (bs, 2H, PhCH2), 3.12 (m, 4H), 3.26 (bs, 2H, PhCH2CH2N), 3.94 (bs, 2H, OCH2), 4.77 (s, 2H, CH2CO2), 7.05 (s, 2Harom), 7.08-7.18 (m, 6Harom), 7.53 (m, 1Harom).

Workup

  1. customThe solvent is evaporated under reduced pressure
  2. customthe crude product is triturated in Et2O (2 ml) until a solid forms
  3. filtrationIt is filtered
  4. washwashed thoroughly with Et2O
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-78c54bb75d924a0796143288b22b1d68
Source dataset
uspto-grants-2012_09
Patent number
US08273740B2

Reaction notes

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