Dimethyl Sulfoxide → HCID 86685160, compound

HRID 1913063Notes

Reaction equation

HRID 1913063 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([O:18][C@H:19]1[C@H:24]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C@@H:23]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C@@:22]([C:43]2[CH:48]=[CH:47][C:46]([CH3:49])=[C:45]([CH2:50][C:51]3[S:52][C:53]([C:56]4[CH:61]=[CH:60][C:59]([F:62])=[CH:58][CH:57]=4)=[CH:54][CH:55]=3)[CH:44]=2)([O:41][CH3:42])[O:21][C@@H:20]1[CH2:63][OH:64])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>ClCCl>[CH2:11]([O:18][C@H:19]1[C@H:24]([O:25][CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C@@H:23]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C@@:22]([C:43]2[CH:48]=[CH:47][C:46]([CH3:49])=[C:45]([CH2:50][C:51]3[S:52][C:53]([C:56]4[CH:57]=[CH:58][C:59]([F:62])=[CH:60][CH:61]=4)=[CH:54][CH:55]=3)[CH:44]=2)([O:41][CH3:42])[O:21][C@@H:20]1[CH:63]=[O:64])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 86685159HCID 86685159, compound

Product 1

HCID 86685160HCID 86685160, compoundYield 101%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-78 °C

Procedure

Oxalyl chloride (0.27 mL, 3.12 mmol) was dissolved in 8 mL dichloromethane and cooled to −78° C. The reaction mixture was stirred for 15 minutes before 4 mL solution of dimethyl sulfoxide (0.36 mL, 5.04 mmol) in dichloromethane were added. Then 8 mL solution of [(2R,3R,4S,5R,6S)-3,4,5-tribenzyloxy-6-[3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4-methyl-phenyl]-6-methoxy-tetrahydropyran-2-yl]methanol 9g (1.8 g, 2.4 mmol) in dichloromethane were dropwise added. The reaction mixture was stirred for 30 minutes. Then triethylamine (1.66 mL, 12 mmol) was added before the reaction mixture was warmed to room temperature and stirred for 1 hour. Thereafter, the reaction mixture was partitioned after 12 mL 1 M hydrochloric acid were added, the organic extract was combined, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure to obtain the title compound (2S,3S,4S,5R,6S)-3,4,5-tribenzyloxy-6-[3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4-methyl-phenyl]-6-methoxy-tetrahydropyran-2-carbaldehyde 9h (1.8 g, yellow grease), which was used directly in the next step without purification.

Workup

  1. additionwere added
  2. temperaturewas warmed to room temperature
  3. stirringstirred for 1 hour
  4. customThereafter, the reaction mixture was partitioned after 12 mL 1 M hydrochloric acid
  5. additionwere added
  6. extractionthe organic extract
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4ef2817e650e4313953ebad7ec949751
Source dataset
uspto-grants-2013_12
Patent number
US08609622B2

Reaction notes

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