Methanol → HCID 66884218, compound

HRID 2204044Notes

Reaction equation

HRID 2204044 reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH3:31])=[CH:25][CH:24]=3)[CH:16]=2)[O:8][C@@H:7](Br)[C@H:6]1[O:33][C:34](=[O:36])[CH3:35])(=[O:3])[CH3:2].[CH3:37][OH:38]>>[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH3:31])=[CH:25][CH:24]=3)[CH:16]=2)[O:8][C@H:7]([O:38][CH3:37])[C@H:6]1[O:33][C:34](=[O:36])[CH3:35])(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 887MethanolHCID 66885751HCID 66885751, compound

Product 1

HCID 66884218HCID 66884218, compoundYield 78%

Conditions

Temperature
70 °C

Procedure

Crude bromide from step B (8.4 g, 14.4 mmol) and ZnO (1.2 g, 14.4 mmol) were dissolved in MeOH (144 ml) and heated at 70° C. for 1 hour. The reaction was cooled to room temperature, filtered through celite with EtOAc, and concentrated under vacuum. The residue was recrystallized from MeOH in two batches to give acetic acid (2S,3S,4R,5S,6S)-4,5-diacetoxy-6-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-2-methoxy-tetrahydro-pyran-3-yl ester (5.98 g, 11.2 mmol, 78%) as the pure β-anomer.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. filtrationfiltered through celite with EtOAc
  3. concentrationconcentrated under vacuum
  4. customThe residue was recrystallized from MeOH in two batches

Sources & evidence

ORD record
ord-fe57ca10cb05402b87629844da0c8f83
Source dataset
uspto-grants-2016_06
Patent number
US09365602B2

Reaction notes

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