Potassium Carbonate → HCID 53892462, Verbindung

HRID 24693Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 24693
[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]

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 178418397HCID 178418397, VerbindungKatalysatorHCID 8857Ethyl AcetateLösungsmittelHCID 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-410ad7b90dea4035828019e4f37d1412
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06855843B2

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