Triethylamine → HCID 58487995, compound

HRID 888223Notes

Reaction equation

HRID 888223 reaction equation
[CH3:1][C:2]1([CH3:27])[O:6][C@@H:5]([C@H:7]([CH2:22][CH:23]([CH3:25])[CH3:24])[C:8]([O:10]C2C(F)=C(F)C(F)=C(F)C=2F)=O)[C:4](=[O:26])[O:3]1.ONC(=O)[C@@H](O)[C@@H](C(N1CCN(C2C=CC=CN=2)CC1)=O)CC(C)C.C(N(CC)CC)C.[CH3:60][C@H:61]1[NH:66][CH2:65][CH2:64][N:63]([C:67]2[CH:72]=[C:71]([C:73]([F:76])([F:75])[F:74])[CH:70]=[CH:69][N:68]=2)[CH2:62]1>CN(C=O)C>[CH3:27][C:2]1([CH3:1])[O:3][C:4](=[O:26])[C@H:5]([C@@H:7]([C:8]([N:66]2[CH2:65][CH2:64][N:63]([C:67]3[CH:72]=[C:71]([C:73]([F:76])([F:74])[F:75])[CH:70]=[CH:69][N:68]=3)[CH2:62][C@H:61]2[CH3:60])=[O:10])[CH2:22][CH:23]([CH3:24])[CH3:25])[O:6]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11653205HCID 11653205, compound2×HCID 58488037HCID 58488037, compound2×HCID 86617975HCID 86617975, compound

Product 1

HCID 58487995HCID 58487995, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 55/45 diastereoisomeric mixture of pentafluorophenyl (2S)-2-[(4S)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]-4-methylpentanoate and pentafluorophenyl (2R)-2-[(4S)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]-4-methylpentanoate (Intermediate 1, 484.8 mg; 1.22 mmol; 1.0 eq.) and triethylamine (339.13 μl; 2.45 mmol; 2.0 eq.) in DMF (10.0 mL) was added (3R)-3-methyl-[4-(trifluoromethyl)pyridin-2-yl]piperazine (Intermediate 9, 300 mg; 1.22 mmol; 1.0 eq.). After 14 h of reaction at RT, the solvent was evaporated and the residue dissolved in ether and extracted with water (3×). The combined organic layers were dried and evaporated to give an oil. This residue was purified by chromatography to give the title product (170 mg; 30.4% as a mixture of 2 diastereoisomers). M+(ESI): 458.4. HPLC (Condition A): Rt: 4.1 min (HPLC purity: 91.8%).

Workup

  1. customAfter 14 h of reaction at RT
  2. customthe solvent was evaporated
  3. dissolutionthe residue dissolved in ether
  4. extractionextracted with water (3×)
  5. customThe combined organic layers were dried
  6. customevaporated
  7. customto give an oil
  8. customThis residue was purified by chromatography

Sources & evidence

ORD record
ord-fca476c66cef4ecea5480bfed2676ea7
Source dataset
uspto-grants-2012_08
Patent number
US08247437B2

Reaction notes

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