Diiodomethane → HCID 57684698, compound

HRID 2403734Notes

Reaction equation

HRID 2403734 reaction equation
[Zn](CC)[CH2:2]C.C(O)(C(F)(F)F)=O.C(I)I.[C:16]([O:19][C@H:20]1[C@H:25]([O:26][C:27](=[O:29])[CH3:28])[C@@H:24]([O:30][C:31](=[O:33])[CH3:32])[C@H:23]([C:34]2[CH:39]=[CH:38][C:37]([Cl:40])=[C:36]([CH2:41][C:42]3[CH:47]=[CH:46][C:45]([C:48]([CH2:50][O:51][CH3:52])=[CH2:49])=[CH:44][CH:43]=3)[CH:35]=2)[O:22][C@@H:21]1[CH2:53][O:54][C:55](=[O:57])[CH3:56])(=[O:18])[CH3:17]>C(Cl)Cl>[C:16]([O:19][C@H:20]1[C@H:25]([O:26][C:27](=[O:29])[CH3:28])[C@@H:24]([O:30][C:31](=[O:33])[CH3:32])[C@H:23]([C:34]2[CH:39]=[CH:38][C:37]([Cl:40])=[C:36]([CH2:41][C:42]3[CH:43]=[CH:44][C:45]([C:48]4([CH2:50][O:51][CH3:52])[CH2:2][CH2:49]4)=[CH:46][CH:47]=3)[CH:35]=2)[O:22][C@@H:21]1[CH2:53][O:54][C:55](=[O:57])[CH3:56])(=[O:18])[CH3:17]

Participants

6

Reactant 4

HCID 6346DiiodomethaneHCID 6422Trifluoroacetic acidHCID 57684699HCID 57684699, compoundHCID 178418750HCID 178418750, compound

Product 1

HCID 57684698HCID 57684698, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a cooled (0° C.) solution of ZnEt2 (0.16 mL, 0.16 mmol) CH2Cl2 (0.4 mL) was added a solution of TFA (12 μL, 0.16 mmol) in CH2Cl2 (0.2 mL). After stirring for 20 min, a solution of CH2I2 (43 mg, 0.16 mmol) in CH2Cl2 (0.2 mL) was added. After stirring for an additional 20 min, a solution of (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-(3-methoxyprop-1-en-2-yl)benzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (intermediate BC) (32 mg, 0.053 mmol) in CH2Cl2 (0.4 mL) was added. The mixture was stirred overnight prior to quenching with a saturated solution of NaHCO3. The mixture was extracted 3× with CH2Cl2, and the organic portion was washed with brine prior to drying over Na2SO4. Concentration of the solution gave crude intermediate BC (25 mg).

Workup

  1. stirringAfter stirring for an additional 20 min
  2. stirringThe mixture was stirred overnight
  3. customto quenching with a saturated solution of NaHCO3
  4. extractionThe mixture was extracted 3× with CH2Cl2
  5. washthe organic portion was washed with brine
  6. dry with materialto drying over Na2SO4
  7. customConcentration of the solution gave crude intermediate BC (25 mg)

Sources & evidence

ORD record
ord-c8afad2282de43d1aec2687aea4dfdf9
Source dataset
uspto-grants-2014_08
Patent number
US08802637B2

Reaction notes

Loading…