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Potassium Carbonate → HCID 53892462, Verbindung

HRID 1060465
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1060465
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][Si](C(C)(C)C)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:6]=[C:5]([O:27][CH3:28])[C:4]=1B(O)O.[CH2:32]([O:34][C:35](=[O:56])[C@H:36]([CH2:48][C:49]1[CH:54]=[CH:53][C:52](Br)=[CH:51][CH:50]=1)[NH:37][C:38](=[O:47])[C:39]1[C:44]([Cl:45])=[CH:43][CH:42]=[CH:41][C:40]=1[Cl:46])[CH3:33].C([O-])([O-])=O.[K+].[K+]>COCCOC.O.CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:32]([O:34][C:35](=[O:56])[C@H:36]([CH2:48][C:49]1[CH:54]=[CH:53][C:52]([C:4]2[C:5]([O:27][CH3:28])=[CH:6][C:7]([OH:9])=[CH:8][C:3]=2[O:2][CH3:1])=[CH:51][CH:50]=1)[NH:37][C:38](=[O:47])[C:39]1[C:40]([Cl:46])=[CH:41][CH:42]=[CH:43][C:44]=1[Cl:45])[CH3:33]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 225718572,6-Dimethoxy-4-(tert-butyl-diphenylsilyloxy)benzeneboronic acidHCID 54106344(S)-Ethyl 3-(4-bromophenyl)-2-(2,6-dichlorobenzamido)propanoate

Produkt 1

HCID 53892462HCID 53892462, VerbindungAusbeute 53,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 8857Ethyl AcetateLösungsmittel
HCID 18180031Water 1,2-dimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 2,6-dimethoxy-4-(tert-butyl-diphenylsilyloxy)benzeneboronic acid (3 g), N-(2,6-dichlorobenzoyl)-4-bromo-L-phenylalanine ethyl ester (0.8 g), Pd(PPh3)4 (1 g) and K2CO3 (2.1 g) in DME/H2O (20 mL/0.5 mL) was heated at 80° C. for 6 hour under N2. The mixture was diluted with EtOAc and washed with water, dried and evaporated. The residue was dissolved in EtOAc and the solution was filtered through a silica gel column and evaporated. The residue was dissolved in THF, and TBAF (1.6 M in THF, 4 ml) was added. The mixture was stirred at room temperature for 1 hour, diluted with water and extracted with EtOAc. The extract was washed with water, dried and evaporated. The residue was purified by flash column chromatography (silica gel; eluent: EtOAc/hexane 1/2) to yield 0.5 g of N-(2,6-dichlorobenzoyl)-4-(2,6-dimethoxy-4-hydroxyphenyl)-L-phenylalanine ethyl ester. ESMS m/z: 490 (MH+).

Aufarbeitung

  1. washwashed with water
  2. customdried
  3. customevaporated
  4. dissolutionThe residue was dissolved in EtOAc
  5. filtrationthe solution was filtered through a silica gel column
  6. customevaporated
  7. dissolutionThe residue was dissolved in THF
  8. additionTBAF (1.6 M in THF, 4 ml) was added
  9. additiondiluted with water
  10. extractionextracted with EtOAc
  11. washThe extract was washed with water
  12. customdried
  13. customevaporated
  14. customThe residue was purified by flash column chromatography (silica gel; eluent: EtOAc/hexane 1/2)

Quellen und Nachweise

ORD-Eintrag
ord-b4192d1d43df45af98c7c5244ced11c1
Quelldatensatz
uspto-grants-2003_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06521666B1

Notizen zur Reaktion

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