Acetyl chloride → HCID 178466087, compound

HRID 339915Notes

Reaction equation

HRID 339915 reaction equation
BO[C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:14]([CH3:16])([CH3:15])[O:13][C:12]([NH:17][C@H:18]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[F:35])[CH2:19][CH2:20][O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])=[N:11][S:10]2(=[O:37])=[O:36])=[CH:5][CH:4]=1.[C:38]([O-])(=[O:40])[CH3:39].[K+].C(Cl)(=O)C>O1CCOCC1.C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[Si:22]([O:21][CH2:20][CH2:19][C@H:18]([NH:17][C:12]1[O:13][C:14]([CH3:15])([CH3:16])[CH:9]([C:6]2[CH:5]=[CH:4][C:3]([C:38](=[O:40])[CH3:39])=[CH:8][CH:7]=2)[S:10](=[O:37])(=[O:36])[N:11]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[F:35])([C:25]([CH3:26])([CH3:28])[CH3:27])([CH3:24])[CH3:23]

Participants

7

Reactant 3

HCID 6367Acetyl chlorideHCID 517044Potassium AcetateHCID 178419233HCID 178419233, compound

Product 1

HCID 178466087HCID 178466087, compoundYield 41.9%

Reagents, catalysts & solvents 3

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of [5-(4-boroxyphenyl)-6,6-dimethyl-4,4-dioxo-5,6-dihydro-4H-4lambda*6*-[1,4,3]oxathiazin-2-yl]-[(S)-3-(tert-butyldimethylsilanyloxy)-1-(2-fluorophenyl)propyl]amine (400 mg) and potassium acetate (140 mg) in dioxane (6 ml) were added bis(triphenylphosphine)palladium(II)dichloride (60 mg) and acetyl chloride (120 μl), and the mixture was stirred at 50° C. overnight. The mixture was diluted with ethyl acetate, washed with water, dried over magnesium sulfate and concentrated. This was followed by purification by column chromatography (ethyl acetate/heptane). This gave the product (172 mg) with a molecular weight of 562.8 g/mol (C28H39FN2O5SSi).

Workup

  1. washwashed with water
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customThis was followed by purification by column chromatography (ethyl acetate/heptane)

Sources & evidence

ORD record
ord-3bdde6afe268461dbd7b8a7b58c9aa19
Source dataset
uspto-grants-2014_11
Patent number
US08895547B2

Reaction notes

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