HCID 86630345, compound → HCID 16043216, compound

HRID 217630Notes

Reaction equation

HRID 217630 reaction equation
C([Si](CC)(CC)[O:4][C@H:5]1[CH2:10][C@H:9]([O:11][Si](CC)(CC)CC)[CH2:8]/[C:7](=[CH:19]/[CH:20]=[C:21]2\[CH2:22][CH2:23][CH2:24][C@@:25]3([CH3:41])[C@H:29]\2[CH2:28][CH2:27][C@@H:26]3[C@@:30]2([CH3:40])[O:34][CH2:33][C@H:32]([CH2:35][C:36]([CH3:39])([OH:38])[CH3:37])[CH2:31]2)/[C:6]1=[CH2:42])C>CC#N.CCN(CC)CC>[OH:38][C:36]([CH3:39])([CH3:37])[CH2:35][C@@H:32]1[CH2:33][O:34][C@@:30]([C@@H:26]2[C@:25]3([CH3:41])[C@H:29](/[C:21](=[CH:20]/[CH:19]=[C:7]4\[C:6](=[CH2:42])[C@@H:5]([OH:4])[CH2:10][C@H:9]([OH:11])[CH2:8]\4)/[CH2:22][CH2:23][CH2:24]3)[CH2:28][CH2:27]2)([CH3:40])[CH2:31]1

Participants

4

Reactant 1

HCID 86630345HCID 86630345, compound

Product 1

HCID 16043216HCID 16043216, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

HF-Py (0.4 mL) was added to a solution of compound 16 (134 mg, 0.2 mmol) in CH3CN (2.5 mL) and Et3N (1.5 mL). After 10 min, the reaction was quenched by the addition of saturated NaHCO3 (5 mL). The mixture was extracted with Et2O (2×20 mL). The combined organic phase was washed with saturated NaCl (25 mL) and H2O (25 mL), dried, filtered and concentrated in vacuum. The residue was purified by flash chromatography (SiO2, 1.5×9.5 cm, 50% EtOAc-hexanes) to give compound A (80 mg, 88%, white solid, mp: 128° C.).

Workup

  1. customthe reaction was quenched by the addition of saturated NaHCO3 (5 mL)
  2. extractionThe mixture was extracted with Et2O (2×20 mL)
  3. washThe combined organic phase was washed with saturated NaCl (25 mL) and H2O (25 mL)
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated in vacuum
  7. customThe residue was purified by flash chromatography (SiO2, 1.5×9.5 cm, 50% EtOAc-hexanes)

Sources & evidence

ORD record
ord-f144a75ada88400db1fb24795773de9c
Source dataset
uspto-grants-2012_06
Patent number
US08198263B2

Reaction notes

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