Trifluoroacetic acid → HCID 86685105, compound

HRID 1912986Notes

Reaction equation

HRID 1912986 reaction equation
[CH2:1]([O:8][C@H:9]1[C@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@@:12]([C:33]2[CH:38]=[CH:37][C:36]([Cl:39])=[C:35]([CH2:40][C:41]3[CH:46]=[CH:45][C:44]([O:47][CH2:48][CH2:49][O:50][CH:51]4[CH2:53][CH2:52]4)=[CH:43][CH:42]=3)[CH:34]=2)([O:31][CH3:32])[O:11][C:10]1(CO)[CH2:54][OH:55])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:1]([O:8][C@H:9]1[C@H:14]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C@@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@:12]2([C:33]3[CH:38]=[CH:37][C:36]([Cl:39])=[C:35]([CH2:40][C:41]4[CH:42]=[CH:43][C:44]([O:47][CH2:48][CH2:49][O:50][CH:51]5[CH2:53][CH2:52]5)=[CH:45][CH:46]=4)[CH:34]=3)[O:11][C@@:10]1([CH2:54][OH:55])[CH2:32][O:31]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86685104HCID 86685104, compound

Product 1

HCID 86685105HCID 86685105, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C

Procedure

[(3S,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-[[4-[2-(cyclopropoxy)ethoxy]phenyl]methyl]phenyl]-2-(hydroxymethyl)-6-methoxy-tetrahydropyran-2-yl]methanol if (320 mg, 0.4 mmol) was dissolved in 10 mL methylene chloride and cooled to −10° C., followed by addition of trifluoroacetic acid (62 mL, 0.8 mmol). The mixture was stirred for 1 hour. Thereafter, the reaction mixture was partitioned after 10 mL saturated sodium bicarbonate solution were added. The aqueous phase was extracted with dichlormethane (10 mL) and the organic extract was washed with saturated sodium chloride solution (10 mL), combined, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure and the resulting residue was purified by silica gel chromatography with elution system B to obtain the title compound [(1S,2S,3S,4R,5S)-2,3,4-tribenzyloxy-5-[4-chloro-3-[[4-[2-(cyclopropoxy)ethoxy]phenyl]methyl]phenyl]-6,8-dioxabicyclo[3.2.1]octan-1-yl]methanol 1g (230 mg, colorless oil), yield: 75.3%. MS m/z (ESI): 780.3 [M+18]. 1H NMR (400 MHz, CDCl3): δ 7.33 (m, 12H), 7.15 (m, 4H), 7.05 (m, 2H), 6.86 (d, 2H), 6.76 (d, 2H), 4.77 (m, 4H), 4.27 (m, 2H), 4.00 (m, 6H), 3.83 (m, 3H), 3.70 (m, 4H), 3.38 (m, 1H), 0.63 (m, 2H), 0.48 (m, 2H).

Workup

  1. customThereafter, the reaction mixture was partitioned after 10 mL saturated sodium bicarbonate solution
  2. additionwere added
  3. extractionThe aqueous phase was extracted with dichlormethane (10 mL)
  4. extractionthe organic extract
  5. washwas washed with saturated sodium chloride solution (10 mL)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. customthe resulting residue was purified by silica gel chromatography with elution system B

Sources & evidence

ORD record
ord-dda8a32311904641816738e8c9750067
Source dataset
uspto-grants-2013_12
Patent number
US08609622B2

Reaction notes

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