Triphenylphosphine → N-(2,2-Diphenylethyl)-N-(2-chloro-3-trifluoromethylbenzyl)-2,2-dimethyl-3-(3-aminopropoxy)phenylpropionic Acid

HRID 229121Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 229121
[CH3:1][C:2](C)([CH2:7][C:8]1C=C[CH:11]=[C:10](O)[CH:9]=1)[C:3]([O:5]C)=[O:4].[C:16]1([CH:22]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH2:23][N:24]([CH2:37][CH2:38][CH2:39][OH:40])[CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[C:27]=2[Cl:36])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(O[CH:77]([CH3:79])[CH3:78])=O)=O)C>C1COCC1.O>[C:41]1([CH:22]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:23][N:24]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:34])([F:35])[F:33])[C:27]=2[Cl:36])[CH2:37][CH2:38][CH2:39][O:40][C:11]2[C:77]([CH3:78])([CH3:79])[CH:7]([CH:2]([CH3:1])[C:3]([OH:5])=[O:4])[CH:8]=[CH:9][CH:10]=2)[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1

Komponenten

7

Edukt 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 577571173-[(2-Chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propan-1-olHCID 67520417Methyl 2,2-dimethyl-3-(3-hydroxyphenyl)propionate

Produkt 1

HCID 68864466N-(2,2-Diphenylethyl)-N-(2-chloro-3-trifluoromethylbenzyl)-2,2-dimethyl-3-(3-aminopropoxy)phenylpropionic AcidAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of methyl 2,2-dimethyl-3-(3-hydroxyphenyl)propionate (135 mg, 0.65 mmol) and N-(2,2-diphenylethyl)-N-(2-chloro-3-trifluoromethylbenzyl)-3-hydroxypropylamine (290 mg, 0.65 mmol) in THF (8 mL) was treated with Ph3P (170 mg, 0.65 mmol), diisopropylazodicarboxylate (135 mg, 0.65 mmol), and stirred for 16 h. The reaction was diluted with H2O and extracted with Et2O. The extracts were washed with H2O, dried, and concentrated. Purification via silica gel column chromatography eluted with 30% EtOAc:hexane yielded the titled compound (200 mg, 50%). MS (ESI) 639 (M+H+).

Aufarbeitung

  1. extractionextracted with Et2O
  2. washThe extracts were washed with H2O
  3. customdried
  4. concentrationconcentrated
  5. customPurification via silica gel column chromatography
  6. washeluted with 30% EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-958175d07f5c4b8c9fbd1e1ffcded43c
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560586B2

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