Diisopropylethylamine → Tert-Butyl 4-(2-(3-formylphenoxy)acetyl)piperazine-1-carboxylate

HRID 592075Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 592075
[CH:1]([C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][CH:13]=1)[O:6][CH2:7][C:8]([OH:10])=O)=[O:2].[N:14]1([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH:1]([C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][CH:13]=1)[O:6][CH2:7][C:8]([N:17]1[CH2:16][CH2:15][N:14]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:19][CH2:18]1)=[O:10])=[O:2]

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 6018952-(3-Formylphenoxy)acetic acid2×HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Produkt 1

HCID 89725867Tert-Butyl 4-(2-(3-formylphenoxy)acetyl)piperazine-1-carboxylateAusbeute 29 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

2-(3-formylphenoxy)acetic acid (48)/(1 eq), tert-butyl piperazine-1-carboxylate (1.5 eq) were taken in DCM to which HATU (1.3 eq) and DIPEA (2 eq) along with cat. DMAP were added and the traction mixture was stirred at rt for 16 h when TLC indicated completion of reaction. The reaction mixture was diluted with DCM and the organic extract was washed with water, dried and purified by column chromatography using silica gel (100-200 mesh) to afford the pure product (29%) as a colorless oil. LCMS: 91.65% (M++1-Boc).

Aufarbeitung

  1. customcompletion of reaction
  2. extractionthe organic extract
  3. washwas washed with water
  4. customdried
  5. custompurified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-92e93f901bf943e08fc2debccf35cc1b
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09238656B2

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