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Triphenylphosphine → HCID 178418455, Verbindung

HRID 1694
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1694
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([O:12][CH3:13])[CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:33]([NH:40][C@H:41]1[CH2:46][CH2:45][C@H:44](O)[CH2:43][CH2:42]1)([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34].N(C(OCC)=O)=N[C:50](OCC)=[O:51]>C1COCC1>[C:33]([NH:40][C@H:41]1[CH2:46][CH2:45][C@@H:44]([C:50]([O:1][C:2]2[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([O:12][CH3:13])[CH:3]=2)=[O:51])[CH2:43][CH2:42]1)([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 12532676Methyl 4-hydroxy-2-methoxybenzoateHCID 178418329HCID 178418329, Verbindung

Produkt 1

HCID 178418455HCID 178418455, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel
2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a stirred solution of methyl 4-hydroxy-2-methoxybenzoate (1.09 g, 6.0 mmol) in dry THF (7 mL) was added triphenylphosphine (1.57 g, 6.0 mmol) and the solution was cooled to 0° C. A 4.0 mL volume of N-Boc-trans-1-amino-4-cyclohexanol (1 g, 4.0 mmol) and diethyl azodicarboxylate (945 μL, 6.0 mmol) in THF was added dropwise via addition funnel over 0.5 h. The reaction was filtered and the solvent was removed under reduced pressure. The residue was chromatographed on a silica gel column packed in 70:30 hexanes:EtOAc and eluted with same. The appropriate fractions were combined and the solvent removed under reduced pressure to afford methyl 4-[N-Boc-cis-1-amino-4-cyclohexanoyloxy]-2-methoxybenzoate.

Aufarbeitung

  1. filtrationThe reaction was filtered
  2. customthe solvent was removed under reduced pressure
  3. customThe residue was chromatographed on a silica gel column
  4. washEtOAc and eluted with same
  5. customthe solvent removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-75cd419ae27e4e64877635a7083429d0
Quelldatensatz
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05726172

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