1-Methylimidazole → HCID 67341044, compound

HRID 330730Notes

Reaction equation

HRID 330730 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@H:13]([OH:14])[C@@H:12]([CH2:15][O:16][C:17]([C:32]2[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=2)([C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[O:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.[C:49]([CH2:51][CH2:52][O:53][P:54](Cl)[N:55]([CH:59]([CH3:61])[CH3:60])[CH:56]([CH3:58])[CH3:57])#[N:50].CN1C=CN=C1>C(Cl)Cl>[CH2:1]([O:8][C@@H:9]1[C@H:13]([O:14][P:54]([O:53][CH2:52][CH2:51][C:49]#[N:50])[N:55]([CH:56]([CH3:57])[CH3:58])[CH:59]([CH3:60])[CH3:61])[C@@H:12]([CH2:15][O:16][C:17]([C:32]2[CH:33]=[CH:34][C:35]([O:38][CH3:39])=[CH:36][CH:37]=2)([C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[O:11][CH2:10]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 13901-MethylimidazoleHCID 81531DiisopropylethylamineHCID 27348442-Cyanoethyl N,N-diisopropylchlorophosphoramiditeHCID 68379568HCID 68379568, compound

Product 1

HCID 67341044HCID 67341044, compoundYield 42.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled solution (0° C.) of 1,4-anhydro-2-O-benzyl-5-O-[bis(4-methoxyphenyl)(phenyl)methyl]D-ribitol (1.60 g, 3.04 mmol) and N,N-diisopropylethylamine (1.59 mL, 9.11 mmol) in DCM (20 mL), 2-cyanoethyl-N,N-diisopropylchlorophosphoramidite (1.44 g, 6.08 mmol) and 1-methylimidazole (0.12 mL, 1.519 mmol) were added. The reaction mixture was warmed to ambient temperature and stirred for 90 min. The reaction was then quenched with methanol (5 mL) and stirred for 5 min. The solvent was then removed in vacuo, and the residue was purified by flash chromatography using 20% ethyl acetate in hexane to obtain 0.94 g (1.293 mmol, 42.6%) of the pure product. LCMS: for C42H51N2O7P calculated 726.3. found 727.3 [M+H]+ and 749.4 [M+Na]+. 31P NMR (400 MHz, CD3CN) δ: 149.94, 149.70.

Workup

  1. customThe reaction was then quenched with methanol (5 mL)
  2. stirringstirred for 5 min
  3. customThe solvent was then removed in vacuo
  4. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-57ace1569bf34018b026787b7523477d
Source dataset
uspto-grants-2014_11
Patent number
US08877439B2

Reaction notes

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