Hydrochloric Acid → HCID 178424540, compound

HRID 339845Notes

Reaction equation

HRID 339845 reaction equation
[Si]([O:8][CH2:9][CH2:10][C@H:11]([NH:18][C:19]1[O:20][C:21]([CH3:35])([CH3:34])[CH:22]([C:27]2[CH:28]=[C:29]([CH3:33])[CH:30]=[CH:31][CH:32]=2)[S:23](=[O:26])(=[O:25])[N:24]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(C(C)(C)C)(C)C.Cl>CO.C(OCC)(=O)C>[CH3:34][C:21]1([CH3:35])[O:20][C:19]([NH:18][C@H:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:10][CH2:9][OH:8])=[N:24][S:23](=[O:26])(=[O:25])[CH:22]1[C:27]1[CH:28]=[C:29]([CH3:33])[CH:30]=[CH:31][CH:32]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 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

Product 1

HCID 178424540HCID 178424540, compoundYield 56.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

51.7 mg of [(S)-3-(tert-butyldimethylsilanyloxy)-1-phenylpropyl]-(6,6-dimethyl-4,4-dioxo-5-m-tolyl-5,6-dihydro-4H-4lambda6-1,4,3-oxathiazin-2-yl)amine were dissolved in 2 ml of methanol, 0.1 ml of concentrated hydrochloric acid was added and the mixture was stirred at room temperature for 16 hours. The reaction solution was diluted with ethyl acetate and washed with saturated aqueous sodium chloride solution, dried over MgSO4 and concentrated by rotary evaporation. The residue was 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 and extracted with dichloromethane. The organic phase was dried over MgSO4 and concentrated by rotary evaporation, and the residue was taken up again in a mixture of acetonitrile and water and lyophilized. This gave the product (22.9 mg) with a molecular weight of 402.5 g/mol (C21H26N2O4S); MS (ESI): m/e=403 (M+H+).

Workup

  1. washwashed with saturated aqueous sodium chloride solution
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated by rotary evaporation
  4. customThe residue was purified in a purification laboratory by means of preparative HPLC
  5. customthe acetonitrile was removed under reduced pressure
  6. extractionextracted with dichloromethane
  7. dry with materialThe organic phase was dried over MgSO4
  8. concentrationconcentrated by rotary evaporation
  9. additionthe residue was taken up again in a mixture of acetonitrile and water

Sources & evidence

ORD record
ord-d98b568cce9e41568631b4be6f64206d
Source dataset
uspto-grants-2014_11
Patent number
US08895547B2

Reaction notes

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