Acetyl chloride → HCID 24764501, compound

HRID 2261199Notes

Reaction equation

HRID 2261199 reaction equation
[Cl:1]C1C=CC([C@H]2[C@H](O)[C@@H](O)[C@H](O)C(OC)O2)=CC=1CC1C=CC(OCC)=CC=1.C(Cl)(C)=O.C([Si](C)(C)[O:38][C@H:39]1[C@H:46]2[C@H:42]([O:43][C:44](C)(C)[O:45]2)[O:41][C@H:40]1[C@H:49]([C:51]1[CH:56]=[CH:55][C:54]([Cl:57])=[C:53]([CH2:58][C:59]2[CH:64]=[CH:63][C:62]([O:65][CH2:66][CH3:67])=[CH:61][CH:60]=2)[CH:52]=1)[OH:50])(C)(C)C>CO>[ClH:1].[Cl:57][C:54]1[CH:55]=[CH:56][C:51]([C@H:49]2[C@H:40]([OH:41])[C@@H:39]([OH:38])[C@H:46]([OH:45])[CH:42]([O:43][CH3:44])[O:50]2)=[CH:52][C:53]=1[CH2:58][C:59]1[CH:60]=[CH:61][C:62]([O:65][CH2:66][CH3:67])=[CH:63][CH:64]=1

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 24764501HCID 24764501, compoundHCID 66884302HCID 66884302, compound

Product 2

HCID 313Hydrochloric AcidHCID 24764501HCID 24764501, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Preparation of (2S,3R,4R,5S)-2-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-6-methoxy-tetrahydro-pyran-3,4,5-triol. 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-f287946cea7a485fa4ea5e5f80838718
Source dataset
uspto-grants-2010_12
Patent number
US07846945B2

Reaction notes

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