Hydrofluoric Acid → HCID 70146110, compound

HRID 1066277Notes

Reaction equation

HRID 1066277 reaction equation
[O:1]([CH:9]([C:39]([F:47])([F:46])[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])[CH2:10][CH2:11][C@H:12]1[C@H:16]([O:17]C2CCCCO2)[CH2:15][C:14](=[O:24])[CH:13]1[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33]([O:35][CH:36]([CH3:38])[CH3:37])=[O:34])[Si](C(C)(C)C)(C)C.F>C(#N)C>[F:46][C:39]([F:47])([CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])[C@H:9]([OH:1])[CH2:10][CH2:11][C@H:12]1[C@H:16]([OH:17])[CH2:15][C:14](=[O:24])[CH:13]1[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33]([O:35][CH:36]([CH3:37])[CH3:38])=[O:34]

Participants

4

Reactant 2

HCID 14917Hydrofluoric AcidHCID 70148841HCID 70148841, compound

Product 1

HCID 70146110HCID 70146110, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The compound (12-11) (0.93 g) was hydrolyzed in acetonitrile (30 ml) with 46% hydrofluoric acid (1.55 ml). The crude product obtained by the conventional treatment was purified by silica gel chromatography (n-hexane/ethyl acetate=7/3-1/1), and the compound obtained was further fractionated by HPLC to give isopropyl 9-{2(R)-4,4-difluoro-3(R)-hydroxydecyl]-3(R)-hydroxy-5-oxocyclopentyl}nonanoate (12-12).

Workup

  1. customThe crude product obtained by the conventional treatment
  2. customwas purified by silica gel chromatography (n-hexane/ethyl acetate=7/3-1/1)
  3. customthe compound obtained

Sources & evidence

ORD record
ord-cd52159d57da460cb7634604aeea3be3
Source dataset
uspto-grants-2001_06
Patent number
US06242485B1

Reaction notes

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