Triethylamine → HCID 86685133, compound

HRID 1913028Notes

Reaction equation

HRID 1913028 reaction equation
C(Cl)(=O)C(Cl)=O.[CH2:7]([O:14][C@H:15]1[C@H:20]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C@@H:19]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C@@:18]([C:39]2[CH:44]=[CH:43][C:42]([Cl:45])=[C:41]([CH2:46][C:47]3[CH:48]=[CH:49][C:50]4[O:54][CH2:53][CH2:52][C:51]=4[CH:55]=3)[CH:40]=2)([O:37][CH3:38])[O:17][C@@H:16]1[CH2:56][OH:57])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(N(CC)CC)C>C(Cl)Cl>[CH2:7]([O:14][C@H:15]1[C@H:20]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C@@H:19]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C@@:18]([C:39]2[CH:44]=[CH:43][C:42]([Cl:45])=[C:41]([CH2:46][C:47]3[CH:48]=[CH:49][C:50]4[O:54][CH2:53][CH2:52][C:51]=4[CH:55]=3)[CH:40]=2)([O:37][CH3:38])[O:17][C@@H:16]1[CH:56]=[O:57])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 68015075HCID 68015075, compound

Product 1

HCID 86685133HCID 86685133, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

Oxalyl chloride (0.76 mL, 8.91 mmol) was dissolved in 10 mL methylene chloride and cooled to −78° C., followed by dropwise addition of 10 mL of mixed solution (methylene chloride and dimethyl sulfoxide, v:v=10:0.85). The reaction mixture was stirred for 15 minutes. Then 25 mL solution of [(2R,3R,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-(2,3-dihydrobenzofuran-5-ylmethyl)phenyl]-6-methoxy-tetrahydropyran-2-yl]methanol 5h (4.2 g, 5.94 mmol) in methylene chloride was dropwise added before the mixture was stirred for 40 minutes. The reaction mixture was warmed to room temperature and stirred for 2 hours after triethylamine (4.29 mL, 29.69 mmol) was dropwise added. Thereafter, the reaction mixture was partitioned after 35 mL 1 M hydrochloric acid were added, the organic extract was washed with saturated sodium chloride solution (35 mL×2), 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-[4-chloro-3-(2,3-dihydrobenzofuran-5-ylmeth-yl)phenyl]-6-methoxy-tetrahydropyran-2-carbaldehyde 51 (4.19 g, pale yellow grease), which was used directly in the next step without purification.

Workup

  1. stirringwas stirred for 40 minutes
  2. temperatureThe reaction mixture was warmed to room temperature
  3. additionwas dropwise added
  4. customThereafter, the reaction mixture was partitioned after 35 mL 1 M hydrochloric acid
  5. additionwere added
  6. extractionthe organic extract
  7. washwas washed with saturated sodium chloride solution (35 mL×2)
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2f9effd656b2429992523e48595d886c
Source dataset
uspto-grants-2013_12
Patent number
US08609622B2

Reaction notes

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