2-Iodoxybenzoic acid → HCID 118377862, compound

HRID 1055590Notes

Reaction equation

HRID 1055590 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])[C:42]=4[F:51])[CH:34]=3)[O:32][C@@:10]1([CH2:52][OH:53])[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>C(OCC)(=O)C>[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])[C:42]=4[F:51])[CH:34]=3)[O:32][C@@:10]1([CH:52]=[O:53])[CH2:11][O:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 1087942-Iodoxybenzoic acidHCID 86685124HCID 86685124, compound

Product 1

HCID 118377862HCID 118377862, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of [(1S,2S,3S,4R,5S)-2,3,4-tribenzyloxy-5-[4-chloro-3-[(4-ethoxy-2,3-difluoro-phenye methyl]phenyl]-6,8-dioxabicyclo[3.2.1]octan-1-yl]methanol 23n (1.36 g, 1.75 mmol) in ethyl acetate (30 mL) was added 2-iodoxybenzoic acid (735 mg, 2.62 mmol) at room temperature. The mixture was refluxed for 20 hours and cooled to room temperature. The reaction mixture was filtered and the filtrate was concentrated in vacuo to give the title compound 23o as a yellow soild (1.32 g, 100%). This material was not further purified.

Workup

  1. temperatureThe mixture was refluxed for 20 hours
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-2441e6ad3d0647029b0d7fb67890cf83
Source dataset
uspto-grants-2016_07
Patent number
US09394329B2

Reaction notes

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