Triethylamine → HCID 59722612, compound

HRID 1664859Notes

Reaction equation

HRID 1664859 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][C:27](=O)[C:28]([CH3:31])([CH3:30])[CH3:29].C(N(CC)CC)C>C(O)C.[Hg](Cl)Cl>[C:28]([C:27]1[N:14]2[CH2:15][C@H:9]([C:3]3[CH:4]=[CH:5][CH:6]=[C:7]([F:8])[C:2]=3[F:1])[CH2:10][CH2:11][C@@H:12]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[C:13]2=[N:25][CH:26]=1)([CH3:31])([CH3:30])[CH3:29]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 4266281-Amino-3,3-dimethylbutan-2-oneHCID 59734935tert-Butyl (3R,6S)-6-(2,3-difluorophenyl)-2-thioxoazepan-3-ylcarbamate

Product 1

HCID 59722612HCID 59722612, compoundYield 119.2%

Reagents, catalysts & solvents 2

HCID 24085Mercuric ChlorideCatalystHCID 702EthanolSolvent

Procedure

Mercury(II) chloride (10 mg, 0.036 mmol) was added to a solution of tert-butyl [(3R,6S)-6-(2,3-difluorophenyl)-2-thioxoazepan-3-yl]carbamate (10 mg, 0.028 mmol), hydrobromide salt of 1-amino-3,3-dimethylbutan-2-one (11 mg, 0.056 mmol), and triethylamine (10 μL, 0.07 mmol) in ethanol (1 mL) at 70° C. After 18 h, the reaction was allowed to cool to ambient temperature. The mixture was filtered and concentrated. Purification by silica gel chromatography (100% dichloromethane→95% dichloromethane/methanol) gave the title compound (14 mg). MS 420.2 (M+1).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. customPurification by silica gel chromatography (100% dichloromethane→95% dichloromethane/methanol)

Sources & evidence

ORD record
ord-c9773d7eaf7d4fe5ad78ed3d0ca87a71
Source dataset
uspto-grants-2011_10
Patent number
US08039460B2

Reaction notes

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