Trimethylaluminum → N-[(1S)-3-[tert-butyl(dimethyl)silyl]oxy-1-phenylpropyl]-6,6-dimethyl-5-(3-methylphenyl)-4,4-dioxo-5H-1,4,3-oxathiazin-2-amine

HRID 339844Notes

Reaction equation

HRID 339844 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:8]2[C:13]([CH3:15])([CH3:14])[O:12][C:11]([NH:16][C@H:17]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:18][CH2:19][O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])=[N:10][S:9]2(=[O:35])=[O:34])[CH:5]=[CH:6][CH:7]=1.[CH3:36][Al](C)C>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].CC(P(C(C)(C)C)C1[CH-]C=CC=1)(C)C.C1C=CC([C-]2C(C3C=CC=CC=3)=C(C3C=CC=CC=3)C(C3C=CC=CC=3)=C2C2C=CC=CC=2)=CC=1.[Fe+2]>[Si:21]([O:20][CH2:19][CH2:18][C@H:17]([NH:16][C:11]1[O:12][C:13]([CH3:15])([CH3:14])[CH:8]([C:4]2[CH:3]=[C:2]([CH3:36])[CH:7]=[CH:6][CH:5]=2)[S:9](=[O:35])(=[O:34])[N:10]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22]

Participants

6

Reactant 2

HCID 16682925TrimethylaluminumHCID 178431688HCID 178431688, compound

Product 1

HCID 178424541N-[(1S)-3-[tert-butyl(dimethyl)silyl]oxy-1-phenylpropyl]-6,6-dimethyl-5-(3-methylphenyl)-4,4-dioxo-5H-1,4,3-oxathiazin-2-amine

Reagents, catalysts & solvents 3

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 12024214Ditert-butyl(cyclopenta-1,3-dien-1-yl)phosphane;iron(2+);(2,3,4,5-tetraphenylcyclopenta-1,4-dien-1-yl)benzeneCatalystHCID 1140TolueneSolvent

Procedure

Under inert gas, 100 mg of [5-(3-bromophenyl)-6,6-dimethyl-4,4-dioxo-5,6-dihydro-4H-4lambda6-1,4,3-oxathiazin-2-yl]-[(S)-3-(tert-butyldimethylsilanyloxy)-1-phenylpropyl]amine, 8 mg of bis(dibenzylideneacetone)palladium and 19.6 mg of 1,2,3,4,5-pentaphenyl-1-(di-tert-butylphosphino)ferrocene were initially charged, dissolved in 3 ml of toluene and stirred at room temperature for 5 minutes. After the addition of 0.17 ml of a 2 N solution of trimethylaluminum, the reaction mixture was stirred at 70° C. for 1.5 hours. After cooling to room temperature, the solvent was removed under reduced pressure and the residue was purified by means of normal phase chromatography using a Flashmaster with an n-heptane/ethyl acetate gradient. The product-containing fractions were combined and concentrated by rotary evaporation. This gave the product (51.7 mg) with a molecular weight of 516.8 g/mol (C27H40N2O4SSi); MS (ESI): m/e=517 (M+H+).

Workup

  1. stirringthe reaction mixture was stirred at 70° C. for 1.5 hours
  2. temperatureAfter cooling to room temperature
  3. customthe solvent was removed under reduced pressure
  4. customthe residue was purified by means of normal phase chromatography
  5. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-ead67bcf20c3452a8d3f18bb268ae084
Source dataset
uspto-grants-2014_11
Patent number
US08895547B2

Reaction notes

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