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Water → 3-(4-(1-(2(S),3-Dihydroxypropanoyl)-1,2,5,6-tetrahydropyrid-4-yl)-3,5-difluorophenyl)-5(S)-pyrazin-2-ylaminomethyloxazolidin-2-one

HRID 8179
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 8179
CC1(C)[O:6][C@H:5]([C:7]([N:9]2[CH2:14][CH2:13][C:12]([C:15]3[C:20]([F:21])=[CH:19][C:18]([N:22]4[CH2:26][C@H:25]([CH2:27][N:28]([C:36]5[CH:41]=[N:40][CH:39]=[CH:38][N:37]=5)C(OC(C)(C)C)=O)[O:24][C:23]4=[O:42])=[CH:17][C:16]=3[F:43])=[CH:11][CH2:10]2)=[O:8])[CH2:4][O:3]1.FC(F)(F)C(O)=O.O>ClCCl>[OH:6][C@@H:5]([CH2:4][OH:3])[C:7]([N:9]1[CH2:14][CH2:13][C:12]([C:15]2[C:20]([F:21])=[CH:19][C:18]([N:22]3[CH2:26][C@H:25]([CH2:27][NH:28][C:36]4[CH:41]=[N:40][CH:39]=[CH:38][N:37]=4)[O:24][C:23]3=[O:42])=[CH:17][C:16]=2[F:43])=[CH:11][CH2:10]1)=[O:8]
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Komponenten

5

Edukt 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 695849013-(4-(1-(2,2-Dimethyl-1,3-dioxolan-4(S)-ylcarbonyl)-1,2,5,6-tetrahydropyrid-4-yl)-3,5-difluorophenyl)-5(R)-(N-(t-butoxycarbonyl)pyrazin-2-ylaminomethyl)oxazolidin-2-one

Produkt 1

HCID 207256613-(4-(1-(2(S),3-Dihydroxypropanoyl)-1,2,5,6-tetrahydropyrid-4-yl)-3,5-difluorophenyl)-5(S)-pyrazin-2-ylaminomethyloxazolidin-2-oneAusbeute 102 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

3-(4-(1-(2,2-Dimethyl-1,3-dioxolan-4(S)-ylcarbonyl)-1,2,5,6-tetrahydropyrid-4-yl)-3,5-difluorophenyl)-5(R)-(N-(t-butoxycarbonyl)pyrazin-2-ylaminomethyl)oxazolidin-2-one (400 mg, 0.65 mM) was dissolved in dichloromethane (4 ml) and treated with trifluoroacetic acid (4 ml) at ambient temperature. After stirring for 30 minutes at ambient temperature, water (0.8 ml) was added, and stirring continued for 2 hours. Solvent was removed, the residue dissolved in methanol (20 ml), and treated with aqueous ammonia to bring the pH to 8; solvent was removed, and the residue chromatographed on a 10 g silica Mega Bond Elut® column, eluting with a gradient increasing in polarity from 5 to 10% methanol in dichloromethane. Relevant fractions were combined and evaporated to give the desired product (315 mg).

Aufarbeitung

  1. stirringstirring
  2. waitcontinued for 2 hours
  3. customSolvent was removed
  4. dissolutionthe residue dissolved in methanol (20 ml)
  5. additiontreated with aqueous ammonia
  6. customsolvent was removed
  7. customthe residue chromatographed on a 10 g silica Mega Bond Elut® column
  8. washeluting with
  9. temperaturea gradient increasing in polarity from 5 to 10% methanol in dichloromethane
  10. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-49445dd07c0c488a8eefec53cc2c09c9
Quelldatensatz
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07087629B2

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