1-Amino-2-butanol → HCID 178459298, compound

HRID 14394

Reaction equation

HRID 14394 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][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.[NH2:25][CH2:26][CH:27]([OH:30])[CH2:28][CH3:29]>C(O)C.[Hg](Cl)Cl>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:9]1[CH2:15][NH:14][C:13](=[N:25][CH2:26][CH:27]([OH:30])[CH2:28][CH3:29])[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

5

Reactant 2

HCID 261071-Amino-2-butanolHCID 59734935tert-Butyl (3R,6S)-6-(2,3-difluorophenyl)-2-thioxoazepan-3-ylcarbamate

Product 1

HCID 178459298HCID 178459298, compoundYield 108.5%

Reagents, catalysts & solvents 2

HCID 24085Mercuric ChlorideCatalystHCID 702EthanolSolvent

Procedure

Mercury(II) chloride (174 mg, 0.640 mmol) was added to a solution of tert-butyl [(3R,6S)-6-(2,3-difluorophenyl)-2-thioxoazepan-3-yl]carbamate (190 mg, 0.533 mmol) and 1-aminobutan-2-ol (152 μL, 1.60 mmol) in ethanol (5 mL) at 55° C. After 30 min, the reaction was allowed to cool to ambient temperature. The mixture was filtered and concentrated. Saturated aqueous sodium carbonate was added and the mixture was extracted with dichloromethane (3×). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated to give the title compound (238 mg). MS 412.2 (M+1).

Workup

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

Sources & evidence

ORD record
ord-f084035ce61e4d8d95185cf8263d086c
Source dataset
uspto-grants-2010_06
Patent number
US07732438B2

Linked notes

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