Acetyl chloride → HCID 24764501, compound

HRID 2204042Notes

Reaction equation

HRID 2204042 reaction equation
C([Cl:4])(C)=O.C([Si](C)(C)[O:10][C@H:11]1[C@H:18]2[C@H:14]([O:15][C:16](C)(C)[O:17]2)[O:13][C@H:12]1[C@H:21]([C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([CH2:30][C:31]2[CH:36]=[CH:35][C:34]([O:37][CH2:38][CH3:39])=[CH:33][CH:32]=2)[CH:24]=1)[OH:22])(C)(C)C>CO>[ClH:4].[Cl:29][C:26]1[CH:27]=[CH:28][C:23]([C@H:21]2[C@H:12]([OH:13])[C@@H:11]([OH:10])[C@H:18]([OH:17])[CH:14]([O:15][CH3:16])[O:22]2)=[CH:24][C:25]=1[CH2:30][C:31]1[CH:32]=[CH:33][C:34]([O:37][CH2:38][CH3:39])=[CH:35][CH:36]=1

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 66884302HCID 66884302, compound

Product 2

HCID 313Hydrochloric AcidHCID 24764501HCID 24764501, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 0.35 M HCl in MeOH was prepared by adding AcCl (0.25 ml, 3.5 mmol) to MeOH (10 ml) and stirring for 15 minutes The alcohol from step D (0.84 g, 1.5 mmol) was treated with this solution for 16 hours at room temperature and 2 hours at 80° C. in a sealed vial. The reaction was cooled to room temperature, quenched with K2CO3 until basic, diluted with CH2Cl2, filtered, and concentrated under vacuum. The product was purified by flash chromatography (40 g SiO2, 0-10% MeOH:CH2Cl2, 60 minutes, 35 ml/min), suspended in H2O, and lyophilized to give (2S,3R,4R,5S)-2-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-6-methoxy-tetrahydro-pyran-3,4,5-triol (0.46 g, 1.1 mmol, 75%) as a white solid. NMR revealed a 1.2:1 ratio of α and β anomers.

Workup

  1. additionwas treated with this solution for 16 hours at room temperature and 2 hours at 80° C. in a sealed vial
  2. customquenched with K2CO3 until basic,
  3. additiondiluted with CH2Cl2
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe product was purified by flash chromatography (40 g SiO2, 0-10% MeOH:CH2Cl2, 60 minutes, 35 ml/min)

Sources & evidence

ORD record
ord-adb6180499404c528a47a74830762a7a
Source dataset
uspto-grants-2016_06
Patent number
US09365602B2

Reaction notes

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