HCID 178418361, compound → HCID 178431679, compound

HRID 339876Notes

Reaction equation

HRID 339876 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2([CH3:36])[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](C(C)(C)C)(C)C)=[N:10][S:9]2(=[O:35])=[O:34])[CH:5]=[CH:6][CH:7]=1.[H][H]>CO.[Pd]>[C:28]1([C@@H:17]([NH:16][C:11]2[O:12][C:13]([CH3:15])([CH3:14])[C:8]([CH3:36])([C:4]3[CH:5]=[CH:6][CH:7]=[CH:2][CH:3]=3)[S:9](=[O:34])(=[O:35])[N:10]=2)[CH2:18][CH2:19][OH:20])[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178431694HCID 178431694, compound

Product 1

HCID 178431679HCID 178431679, compoundYield 67.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Under inert gas, 50 mg of [5-(3-bromophenyl)-5,6,6-trimethyl-4,4-dioxo-5,6-dihydro-4H-4lambda6-1,4,3-oxathiazin-2-yl]-[(S)-3-(tert-butyldimethylsilanyloxy)-1-phenylpropyl]amine were initially charged in 4 ml of methanol and, with addition of 18 mg of 10% Pd/C, a gentle hydrogen stream was passed through for 1 hour. The reaction solution was concentrated by rotary evaporation and the residue purified in a purification laboratory by means of preparative HPLC. The product-containing fractions were combined, the acetonitrile was removed under reduced pressure, and the aqueous residue was basified with saturated aqueous sodium hydrogencarbonate solution. Subsequently, this aqueous residue was extracted with ethyl acetate, and the combined organic phases were dried over MgSO4 and concentrated by rotary evaporation. The residue was taken up again in a mixture of acetonitrile and water and lyophilized. This gave the product (22.8 mg) with a molecular weight of 402.5 g/mol (C21H26N2O4S); MS (ESI): m/e=403 (M+H+).

Workup

  1. customwas passed through for 1 hour
  2. concentrationThe reaction solution was concentrated by rotary evaporation
  3. customthe residue purified in a purification laboratory by means of preparative HPLC
  4. customthe acetonitrile was removed under reduced pressure
  5. extractionSubsequently, this aqueous residue was extracted with ethyl acetate
  6. dry with materialthe combined organic phases were dried over MgSO4
  7. concentrationconcentrated by rotary evaporation
  8. additionThe residue was taken up again in a mixture of acetonitrile and water

Sources & evidence

ORD record
ord-13a87431f6e2410d905be4a1d5e2dd5f
Source dataset
uspto-grants-2014_11
Patent number
US08895547B2

Reaction notes

Loading…