Hydrochloric Acid → HCID 178431673, compound

HRID 339861Notes

Reaction equation

HRID 339861 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]([OH: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>[OH: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]([OH:33])[CH:30]=[CH:31][CH:32]=2)[S:23](=[O:25])(=[O:26])[N:24]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178431689HCID 178431689, compound

Product 1

HCID 178431673HCID 178431673, compoundYield 54.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To detach the protecting group, 150 mg of 3-{2-[(S)-3-(tert-butyldimethylsilanyloxy)-1-phenylpropylamino]-6,6-dimethyl-4,4-dioxo-5,6-dihydro-4H-4lambda6-1,4,3-oxathiazin-5-yl}phenol were dissolved in 3 ml of methanol and, after addition of 0.3 ml of concentrated hydrochloric acid, stirred at room temperature for 16 hours. The reaction solution was concentrated by rotary evaporation and coevaporated twice more with 10 ml of toluene, and 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. Subsequently, this aqueous residue was extracted with dichloromethane, and the combined organic phases were dried using a phase separator cartridge (Chromabond® PTS) and concentrated by rotary evaporation. The residue was taken up again in a mixture of acetonitrile and water and lyophilized. This gave the product (64.2 mg) with a molecular weight of 404.5 g/mol (C20H24N2O5S); MS (ESI): m/e=405 (M+H+).

Workup

  1. concentrationThe reaction solution was concentrated by rotary evaporation
  2. customthe residue was purified in a purification laboratory by means of preparative HPLC
  3. customthe acetonitrile was removed under reduced pressure
  4. extractionSubsequently, this aqueous residue was extracted with dichloromethane
  5. customthe combined organic phases were dried
  6. concentrationconcentrated by rotary evaporation
  7. additionThe residue was taken up again in a mixture of acetonitrile and water

Sources & evidence

ORD record
ord-b1847b97628a4fff946fabf22f70f50e
Source dataset
uspto-grants-2014_11
Patent number
US08895547B2

Reaction notes

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