Diiodomethane → HCID 71243330, compound

HRID 2201665Notes

Reaction equation

HRID 2201665 reaction equation
[CH2:1]([Zn]CC)C.C(O)(C(F)(F)F)=O.ICI.[CH2:16]=[C:17]1[CH2:22][CH2:21][CH:20]([CH2:23][NH:24][C:25](=[O:34])[O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:19][CH2:18]1.[Cl-].[NH4+]>C(Cl)Cl>[CH2:1]1[C:17]2([CH2:22][CH2:21][CH:20]([CH2:23][NH:24][C:25](=[O:34])[O:26][CH2:27][C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH2:19][CH2:18]2)[CH2:16]1

Participants

7

Reactant 5

HCID 6346DiiodomethaneHCID 6422Trifluoroacetic acidHCID 25517Ammonium ChlorideHCID 86723565HCID 86723565, compoundHCID 178418750HCID 178418750, compound

Product 1

HCID 71243330HCID 71243330, compoundYield 86.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Diethyl zinc (25 mL, 1M hexane solution) was slowly added to 100 mL of anhydrous DCM at −40° C. under nitrogen, and further slowly added TFA (2.85 g, 0.025 mol) and reacted for 0.5 h, then diiodomethane (6.67 g, 0.025 mol) was slowly added thereto. The reaction was continued for 0.5 h, then Compound 8-4 (3 g, 0.012 mol) was dissolved in 20 mL of anhydrous DCM and added dropwise to the reaction mixture under nitrogen, reacted overnight at −5° C., added saturated ammonium chloride solution to quench the reaction, followed by liquid separated, the organic phase was concentrated and purified by column chromatography (petroleum ether/ethyl acetate=10:1) to give Compound 8-5 as a white solid (2.85 g, yield 86.9%).

Workup

  1. additionadded dropwise to the reaction mixture under nitrogen
  2. customreacted overnight at −5° C.
  3. customto quench
  4. customthe reaction
  5. customseparated
  6. concentrationthe organic phase was concentrated
  7. custompurified by column chromatography (petroleum ether/ethyl acetate=10:1)

Sources & evidence

ORD record
ord-d1bc944cc7214d48a9334992bdf00e3b
Source dataset
uspto-grants-2016_06
Patent number
US09365499B2

Reaction notes

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