Water → HCID 58487946, compound

HRID 888227Notes

Reaction equation

HRID 888227 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.ONC(=O)[C@@H](O)[C@@H](C([N:64]1[CH2:69][CH2:68][N:67]([C:70]2[CH:75]=[CH:74][CH:73]=[CH:72][N:71]=2)[CH2:66][C@H:65]1[CH3:76])=O)CC(C)C.O>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:64]2[CH2:69][CH2:68][N:67]([C:70]3[CH:75]=[CH:74][CH:73]=[CH:72][N:71]=3)[CH2:66][C@@H:65]2[CH3:76])=[O:10])[CH2:22][CH:23]([CH3:24])[CH3:25])[O:6]1

Participants

6

Reactant 4

HCID 962WaterHCID 11653205HCID 11653205, compound2×HCID 11660575HCID 11660575, compound2×HCID 86617975HCID 86617975, compound

Product 1

HCID 58487946HCID 58487946, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 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, 198 mg; 0.50 mmol; 1.0 eq.) in DMF (4 mL) was added (3S)-3-methyl-1-pyridin-2-ylpiperazine (Intermediate 4, 88.6 mg; 0.50 mmol; 1.0 eq.) and the resulting reaction mixture was stirred 48 h at RT. Water was added and the mixture was extracted with Et2O. The combined organic layers were washed with brine, dried over MgSO4, filtered and evaporated to give an oil. Purification by chromatography (SiO2, gradient from 10% EtOAc in c-hex up to 40% EtOAc in c-hex in 15 min) gave the title compound as a colorless oil (43 mg; 22%) (mixture of 2 diastereoisomers). M+(ESI): 390.3.

Workup

  1. customthe resulting reaction mixture
  2. extractionthe mixture was extracted with Et2O
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customto give an oil
  8. customPurification by chromatography (SiO2, gradient from 10% EtOAc in c-hex up to 40% EtOAc in c-hex in 15 min)

Sources & evidence

ORD record
ord-378867e068f1410a8ef7f638b4852310
Source dataset
uspto-grants-2012_08
Patent number
US08247437B2

Reaction notes

Loading…