Dimethyl Sulfoxide → HCID 86595162, compound

HRID 1829817Notes

Reaction equation

HRID 1829817 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[Si:11]([O:18][C@H:19]([C@H:21]([N:25]1[CH:29]=[C:28]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[N:27]=[CH:26]1)[CH2:22][CH2:23][OH:24])[CH3:20])([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12].C(N(CC)CC)C>C(Cl)Cl.O>[Si:11]([O:18][C@H:19]([C@H:21]([N:25]1[CH:29]=[C:28]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[N:27]=[CH:26]1)[CH2:22][CH:23]=[O:24])[CH3:20])([C:14]([CH3:17])([CH3:15])[CH3:16])([CH3:13])[CH3:12]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 69527792HCID 69527792, compound

Product 1

HCID 86595162HCID 86595162, compoundYield 93.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

Under N2, a cold (−75° C.) solution of oxalyl chloride (285 mg, 2.24 mmol) in CH2Cl2 (10 ml) was treated with DMSO (0.215 ml, 3.03 mmol) and stirred for 10 min. A solution of ethyl 1-[(2S,3R)-2-(tert-butyldimethylsilyloxy)-5-hydroxy-3-pentyl]imidazole-4-carboxylate (400 mg, 1.12 mmol) in CH2Cl2 (5 ml) was slowly added, the resulting mixture was stirred for 50 min at −75 to −45° C. and finally treated with triethylamine (0.59 ml). The reaction mixture was allowed to warm to 0° C., hydrolyzed with water (10 ml) and extracted with CH2Cl2 (20 ml×2). The combined organic layers were dried over sodium sulfate and evaporated in vacuo. The residue was purified by silica gel (13 g) chromatography eluting with chloroform/methanol (100:1) to give ethyl 1-[(2S,3R)-2-(tert-butyldimethylsilyloxy)-5-oxo-3-pentyl]imidazole-4-carboxylate (370 mg, 93%) as a colorless syrup.

Workup

  1. stirringthe resulting mixture was stirred for 50 min at −75 to −45° C.
  2. extractionextracted with CH2Cl2 (20 ml×2)
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by silica gel (13 g) chromatography
  6. washeluting with chloroform/methanol (100:1)

Sources & evidence

ORD record
ord-daa1e85deb4c497ab8d4f0508ed197d6
Source dataset
uspto-grants-2006_06
Patent number
US07064144B2

Reaction notes

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