2-Iodoxybenzoic acid → HCID 117929159, compound

HRID 1055560Notes

Reaction equation

HRID 1055560 reaction equation
[CH2:1]([O:8][C@H:9]1[C@H:15]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C@@H:14]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C@:13]2([C:33]3[CH:38]=[CH:37][C:36]([Cl:39])=[C:35]([CH2:40][C:41]4[CH:46]=[CH:45][C:44]([O:47][CH2:48][CH3:49])=[C:43]([F:50])[CH:42]=4)[CH:34]=3)[O:32][C@@:10]1([CH2:51][OH:52])[CH2:11][O:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I(C1C=CC=CC=1C(O)=O)(=O)=O>ClCCl>[CH2:1]([O:8][C@H:9]1[C@H:15]([O:16][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C@@H:14]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C@:13]2([C:33]3[CH:38]=[CH:37][C:36]([Cl:39])=[C:35]([CH2:40][C:41]4[CH:46]=[CH:45][C:44]([O:47][CH2:48][CH3:49])=[C:43]([F:50])[CH:42]=4)[CH:34]=3)[O:32][C@@:10]1([CH:51]=[O:52])[CH2:11][O:12]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 1087942-Iodoxybenzoic acidHCID 86685130HCID 86685130, compound

Product 1

HCID 117929159HCID 117929159, compoundYield 86.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [(1S,2S,3S,4R,5S)-2,3,4-tribenzyloxy-5-[4-chloro-3-[(4-ethoxy-3-fluoro-phenyl) methyl]phenyl]-6,8-dioxabicyclo[3.2.1]octane-1-yl]methanol 19a (3.48 g, 4.8 mmol, purchased from Shanghai Caerulum Pharma Discovery Co., Ltd.) in dichloromethane (100 mL) was added 2-iodoxybenzoic acid (2.68 g, 9.6 mmol) at room temperature. The mixture was refluxed for 16 hours and filtered. The filtrate was partitioned and the organic layer was adjusted with saturated aqueous sodium bicarbonate to pH 7. The mixture was extracted with dichloromethane (250 mL×2). The combined organic layers were washed with water (100 mL×2) and saturated brine (100 mL×2) in turn, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo. The residue was purified by silica gel chromatography eluted with PE/EtOAc(v/v)=10/1 to give the title compound 19b as yellow oil (3 g, 86.4%). The compound was characterized by the following spectroscopic data: 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.79 (s, 1H), 7.50 (m, 3H), 7.25 (m, 13H), 7.02 (d, 1H), 6.95 (m, 1H), 6.87 (d, 1H), 6.81 (m, 2H), 4.71 (m, 4H), 4.29 (m, 1H), 4.17 (m, 1H), 4.00 (m, 5H), 3.75 (m, 3H), 3.41 (m, 1H), 1.29 (t, 3H).

Workup

  1. temperatureThe mixture was refluxed for 16 hours
  2. filtrationfiltered
  3. customThe filtrate was partitioned
  4. extractionThe mixture was extracted with dichloromethane (250 mL×2)
  5. washThe combined organic layers were washed with water (100 mL×2) and saturated brine (100 mL×2) in turn
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated in vacuo
  9. customThe residue was purified by silica gel chromatography
  10. washeluted with PE/EtOAc(v/v)=10/1

Sources & evidence

ORD record
ord-bb8d8bd7ab0b419f801b7bd8ab8c7015
Source dataset
uspto-grants-2016_07
Patent number
US09394329B2

Reaction notes

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