Imidazole → HCID 67534465, compound

HRID 1616992Notes

Reaction equation

HRID 1616992 reaction equation
[I:1]I.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N1C=CN=C1.[C:27]([O:35][C@H:36]1[C:40]([F:42])([F:41])[CH:39](O)[O:38][C@@H:37]1[CH2:44][O:45][C:46]([C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1)([C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>ClCCl.CCCCCC>[C:27]([O:35][C@H:36]1[C:40]([F:42])([F:41])[CH:39]([I:1])[O:38][C@@H:37]1[CH2:44][O:45][C:46]([C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1)([C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 67534390HCID 67534390, compound

Product 1

HCID 67534465HCID 67534465, compoundYield 113.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent3×HCID 8058HexaneSolvent

Procedure

I2 (0.524 g) and dichloromethane (8 mL) were charged into a round bottom flask in the dark. To this solution was added dropwise a solution of Ph3P (0.634 g) in dichloromethane (8 mL) at ambient temperature. The resulting suspension was stirred at this temperature for 30 minutes and imidazole (0.734 g) was added. After the resulting suspension was stirred for 5 minutes at room temperature, a solution of lactol 8 (0.8 g) in dichloromethane (8 mL) was added dropwise and the resulting solution was stirred overnight at room temperature. Hexane (30 mL) was added and then the suspension was stirred for 10 minutes, filtered, and concentrated to give 1.1 g of (2R,3R)-4,4-difluoro-5-iodo-2-(trityloxymethyl)tetrahydrofuran-3-yl benzoate 10.

Workup

  1. stirringAfter the resulting suspension was stirred for 5 minutes at room temperature
  2. stirringthe resulting solution was stirred overnight at room temperature
  3. stirringthe suspension was stirred for 10 minutes
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e3e9a4a3bb514c5281fee4f8c274fdd8
Source dataset
uspto-grants-2014_07
Patent number
US08765933B2

Reaction notes

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