Hydrochloric Acid → HCID 178431665, compound

HRID 339875Notes

Reaction equation

HRID 339875 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([CH3:37])[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][C:29]=3[F:34])[CH2:18][CH2:19][O:20][Si](C(C)(C)C)(C)C)=[N:10][S:9]2(=[O:36])=[O:35])[CH:5]=[CH:6][CH:7]=1.Cl>CO>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([CH3:37])[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][C:29]=3[F:34])[CH2:18][CH2:19][OH:20])=[N:10][S:9]2(=[O:36])=[O:35])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 1784316875-(3-bromophenyl)-N-[(1S)-3-[tert-butyl(dimethyl)silyl]oxy-1-(2-fluorophenyl)propyl]-5,6,6-trimethyl-4,4-dioxo-1,4,3-oxathiazin-2-amine

Product 1

HCID 178431665HCID 178431665, compoundYield 62.7%

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-(2-fluorophenyl)propyl]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 2.5 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 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 (10.2 mg) with a molecular weight of 499.4 g/mol (C21H24BrFN2O4S); MS (ESI): m/e=500 (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. dry with materialthe combined organic phases were dried over MgSO4
  6. concentrationconcentrated by rotary evaporation
  7. additionThe residue was taken up again in a mixture of acetonitrile and water

Sources & evidence

ORD record
ord-6be1708eb05d4cc7b1e4531fa5cb351b
Source dataset
uspto-grants-2014_11
Patent number
US08895547B2

Reaction notes

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