Triethylamine → HCID 178453873, compound

HRID 1664861Notes

Reaction equation

HRID 1664861 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C@H:9]1[CH2:15][NH:14][C:13](=S)[C@H:12]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:11][CH2:10]1.[Cl-].[F:26][C:27]([F:34])([F:33])[CH2:28][CH:29]([OH:32])[CH2:30][NH3+:31].C(N(CC)CC)C>C(O)C.[Hg](Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C@H:9]1[CH2:15][NH:14]/[C:13](=[N:31]\[CH2:30][CH:29]([OH:32])[CH2:28][C:27]([F:34])([F:33])[F:26])/[C@H:12]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:11][CH2:10]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 59722652HCID 59722652, compoundHCID 866167544,4,4-Trifluoro-2-hydroxybutan-1-aminium chloride

Product 1

HCID 178453873HCID 178453873, compound

Reagents, catalysts & solvents 2

HCID 24085Mercuric ChlorideCatalystHCID 702EthanolSolvent

Procedure

Mercury(II) chloride (538 mg, 1.98 mmol) was added to a solution of tert-butyl [(3R,6S)-6-(2,6-difluorophenyl)-2-thioxoazepan-3-yl]carbamate (353 mg, 0.99 mmol), 4,4,4-trifluoro-2-hydroxybutan-1-aminium chloride (498 mg, 2.77 mmol), and triethylamine (0.61 mL, 4.36 mmol) in ethanol (10 mL) at 55° C. After 2 h, the reaction was allowed to cool to ambient temperature. The mixture was filtered and concentrated. Saturated aqueous sodium bicarbonate was added and the mixture was extracted with dichloromethane (2×). The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated to give the title compound. MS 466.2 (M+1).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. additionSaturated aqueous sodium bicarbonate was added
  4. extractionthe mixture was extracted with dichloromethane (2×)
  5. dry with materialThe combined organic extracts were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-6611fbef944648fe97e802705b3286ad
Source dataset
uspto-grants-2011_10
Patent number
US08039460B2

Reaction notes

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