Hydrochloric Acid → HCID 178431678, compound

HRID 339872Notes

Reaction equation

HRID 339872 reaction equation
[Br:1][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.Cl>CO>[Br:1][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:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH2:18][CH2:19][OH:20])=[N:10][S:9]2(=[O:35])=[O:34])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178431694HCID 178431694, compound

Product 1

HCID 178431678HCID 178431678, compoundYield 63.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To detach the protecting group, 20 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 dissolved in 1 ml of methanol and, after addition of 0.05 ml of concentrated hydrochloric acid, the mixture was stirred at room temperature for 2 hours. 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 using a cartridge containing diatomaceous earth (Varian Chem Elut®) and concentrated by rotary evaporation. The residue was taken up again in a mixture of acetonitrile and water and lyophilized. This gave the product (10.2 mg) with a molecular weight of 481.4 g/mol (C21H25BrN2O4S); MS (ESI): m/e=482 (M+H+).

Workup

  1. concentrationThe reaction solution was concentrated by rotary evaporation
  2. customthe residue 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 ethyl acetate
  5. customthe combined organic phases were dried
  6. additioncontaining diatomaceous earth (Varian Chem Elut®)
  7. concentrationconcentrated by rotary evaporation
  8. additionThe residue was taken up again in a mixture of acetonitrile and water

Sources & evidence

ORD record
ord-6c54b23e1a9e444292ed0cf27008803f
Source dataset
uspto-grants-2014_11
Patent number
US08895547B2

Reaction notes

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