Acetyl chloride → L-Xylopyranoside, methyl 5-C-[4-chloro-3-[(2,3-dihydro-1,4-benzodioxin-6-yl)methyl]phenyl]-, (5S)-

HRID 576430Notes

Reaction equation

HRID 576430 reaction equation
C([Cl:4])(C)=O.[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([C@H:12]([OH:24])[C@@H:13]2[O:20][C@@H:19]3[C@@H:15]([O:16][C:17](C)(C)[O:18]3)[C@@H:14]2[OH:23])=[CH:8][C:7]=1[CH2:25][C:26]1[CH:35]=[CH:34][C:29]2[O:30][CH2:31][CH2:32][O:33][C:28]=2[CH:27]=1>CO>[ClH:4].[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([C@H:12]2[C@H:13]([OH:20])[C@@H:14]([OH:23])[C@H:15]([OH:16])[CH:19]([O:18][CH3:17])[O:24]2)=[CH:8][C:7]=1[CH2:25][C:26]1[CH:35]=[CH:34][C:29]2[O:30][CH2:31][CH2:32][O:33][C:28]=2[CH:27]=1

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 86714092HCID 86714092, compound

Product 2

HCID 313Hydrochloric AcidHCID 71110537L-Xylopyranoside, methyl 5-C-[4-chloro-3-[(2,3-dihydro-1,4-benzodioxin-6-yl)methyl]phenyl]-, (5S)-Yield 48%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 0.35M HCl in CH3OH was prepared by adding AcCl (25 μL, 0.35 mmol) to CH3OH (1.0 mL) at 0° C., and stirring for 15 min. Compound 136 (50 mg, 0.11 mmol) was treated with this solution for 2 h at 80° C. in a sealed vial. The reaction mixture cooled to room temperature, and quenched with K2CO3 until basic. The mixture was diluted with CH2Cl2, filtered, and concentrated in vacuo. The crude was purified by preparative HPLC (reverse phase) to provide the title compound (22 mg, 48%) as a white solid.

Workup

  1. customquenched with K2CO3 until basic
  2. additionThe mixture was diluted with CH2Cl2
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude was purified by preparative HPLC (reverse phase)

Sources & evidence

ORD record
ord-08ad0740c1264f5aaeb6aaf123e3f482
Source dataset
uspto-grants-2015_05
Patent number
US09034921B2

Reaction notes

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