Imidazole → HCID 89287803, compound

HRID 1410306Notes

Reaction equation

HRID 1410306 reaction equation
[Cl:1][C:2]1[C:3]([CH2:47][C:48]2[CH:53]=[CH:52][C:51]([O:54][CH2:55][CH3:56])=[CH:50][CH:49]=2)=[CH:4][C:5]([C@H:9]2[C@H:14]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C@@H:13]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C@H:12]([O:31][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C@@H:11]([CH2:39][O:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45]O)[O:10]2)=[C:6]([OH:8])[CH:7]=1.N1C=CN=C1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[I:81]I>C1C=CC=CC=1.C(OCC)C>[Cl:1][C:2]1[C:3]([CH2:47][C:48]2[CH:53]=[CH:52][C:51]([O:54][CH2:55][CH3:56])=[CH:50][CH:49]=2)=[CH:4][C:5]([C@H:9]2[C@H:14]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C@@H:13]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C@H:12]([O:31][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C@@H:11]([CH2:39][O:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][I:81])[O:10]2)=[C:6]([OH:8])[CH:7]=1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 71117151HCID 71117151, compound

Product 1

HCID 89287803HCID 89287803, compoundYield 93.1%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 5-chloro-4-(4-ethoxybenzyl)-2-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-((5-hydroxypentyloxy)methyl)tetrahydro-2H-pyran-2-yl)phenol (30, 459 mg, 0.58 mmol) in benzene (3 mL) under an atmosphere of nitrogen were added imidazole (448 mg, 1.76 mmol) and triphenylphosphine (467 mg, 1.76 mmol). After 5 min, iodine (448 mg, 1.76 mmol) in benzene (2 mL) was added dropwide to the reaction mixture at room temperature. The reaction solution was stirred for 1 h, diluted with diethyl ether, quenched with saturated sodium hydrogen carbonate, extracted with diethyl ether (2×). The organic layer was washed with brine, dried over magnesium sulfate, filtered and evaporated in vacuo. The resulting crude residue was purified on a Biotage® purification apparatus (silica gel, 5 to 25% tetrahydrofuran in hexanes gradient) to yield the title compound (31, 485 mg, 0.54 mmol, 93%) as yellow foam.

Workup

  1. customquenched with saturated sodium hydrogen carbonate
  2. extractionextracted with diethyl ether (2×)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe resulting crude residue was purified on a Biotage® purification apparatus (silica gel, 5 to 25% tetrahydrofuran in hexanes gradient)

Sources & evidence

ORD record
ord-231ce346874f49cfaa6fdac2cbe97b38
Source dataset
uspto-grants-2014_12
Patent number
US08921412B2

Reaction notes

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