1,2-Dichloroethane → 2-(4-Adamantan-1-yl-phenoxymethyl)-benzoxazole-5-carboxylic acid dimethylamide

HRID 1945479Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1945479
[C:1]12([C:11]3[CH:30]=[CH:29][C:14]([O:15][CH2:16][C:17]4[O:18][C:19]5[CH:25]=[CH:24][C:23]([C:26]([OH:28])=O)=CC=5N=4)=[CH:13][CH:12]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C([NH2:37])C1OC=CC=1.[CH2:38](Cl)[CH2:39]Cl.C1C=CC2N(O)N=NC=2C=1.C[CH2:53][N:54]([CH:58](C)C)C(C)C>CN(CC1C=C(CN(C)C)C(O)=C(CN(C)C)C=1)C>[CH3:53][N:54]([CH3:58])[C:26]([C:23]1[CH:24]=[CH:25][C:19]2[O:18][C:17]([CH2:16][O:15][C:14]3[CH:29]=[CH:30][C:11]([C:1]45[CH2:8][CH:7]6[CH2:9][CH:3]([CH2:4][CH:5]([CH2:6]6)[CH2:10]4)[CH2:2]5)=[CH:12][CH:13]=3)=[N:37][C:38]=2[CH:39]=1)=[O:28]

Komponenten

7

Edukt 5

HCID 111,2-DichloroethaneHCID 3438FurfurylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 249665342-(4-Adamantan-1-yl-phenoxymethyl)-benzoxazole-5-carboxylic acid

Produkt 1

HCID 249668972-(4-Adamantan-1-yl-phenoxymethyl)-benzoxazole-5-carboxylic acid dimethylamideAusbeute 95,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 70262,4,6-Tris((dimethylamino)methyl)phenolLösungsmittel

Versuchsvorschrift

To solution of 2-(4-adamantan-1-yl-phenoxymethyl)-benzoxazole-5-carboxylic acid (30.1 mg, 0.08 mmol), furfuryl amine (11.0 mg, 0.12 mmol, 0.01 ml), EDC (21.7 mg, 0.12 mmol) and HOBt (15.4 mg, 0.12 mmol) in DMF 3.0 mL was added DIPEA (14.2 mg, 0.12 mmol, 0.02 ml). After string at room temperature, the mixture was partitioned between ethyl acetate and brine. The organic phase was dried (MgSO4 anh), and concentrated. The residue was purified by silica gel column chromatography (n-Hexane:EtOAc:MeOH=6:3:1) to give 2-(4-adamantan-1-yl-phenoxymethyl)-benzoxazole-5-carboxylic acid dimethylamide as a white solid (32.9 mg, 90.9% yield).

Aufarbeitung

  1. customAfter string at room temperature, the mixture was partitioned between ethyl acetate and brine
  2. dry with materialThe organic phase was dried (MgSO4 anh)
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography (n-Hexane:EtOAc:MeOH=6:3:1)

Quellen und Nachweise

ORD-Eintrag
ord-7ab7cd6ccbd24ca99f72be340fac1f4f
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08394799B2

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