Potassium Carbonate → {4-[4-(2-{Benzyl-[2-(4-benzyloxy-3-formylaminophenyl)-2-(R)-hydroxyethyl]amino}-ethoxy)phenyl]butyl}carbamic acid benzyl ester

HRID 1696831Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1696831
[CH2:1]([O:8][C:9](=[O:32])[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][NH:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:17][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:33]([O:40][C:41]1[CH:46]=[CH:45][C:44]([C@@H:47]([OH:50])[CH2:48]Br)=[CH:43][C:42]=1[NH:51][CH:52]=[O:53])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C([O-])([O-])=O.[K+].[K+]>O1CCCC1>[CH2:1]([O:8][C:9](=[O:32])[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:16]=[CH:17][C:18]([O:21][CH2:22][CH2:23][N:24]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:48][C@@H:47]([C:44]2[CH:45]=[CH:46][C:41]([O:40][CH2:33][C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)=[C:42]([NH:51][CH:52]=[O:53])[CH:43]=2)[OH:50])=[CH:19][CH:20]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 11142645(R)-N-[5-(2-Bromo-1-hydroxyethyl)-2-(phenylmethoxy)phenyl]formamideHCID 58100148{4-[4-(2-Benzylaminoethoxy)phenyl]butyl}carbamic acid benzyl ester

Produkt 1

HCID 58100114{4-[4-(2-{Benzyl-[2-(4-benzyloxy-3-formylaminophenyl)-2-(R)-hydroxyethyl]amino}-ethoxy)phenyl]butyl}carbamic acid benzyl esterAusbeute 50,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Benzylamine 16 (619 mg, 1.43 mmol) was added to a suspension of bromoalcohol 5 (500 mg, 1.43 mmol) and K2CO3 (495 mg, 3.58 mmol) methanol (10 mL) and tetrahydrofuran (5 mL). The suspension was stirred at ambient temperature for 15 h, then heated to 55° C. for 75 h. The solid was vacuum filtered and the filtrate was concentrated under vacuum. The resulting oil was subjected to column chromatography eluting with 5-50% ethyl acetate in hexanes to afford the desired product 17 (508 mg, 5%) as an off-white solid: 1H NMR (500 MHz, CDCl3) δ 1.45-1.62 (m, 4H), 2.54 (t, 2H), 2.65-2.71 (m, 1H), 3.14-3.23 (m, 3H), 3.58-3.74 (m, 1H), 3.88-4.09 (m, 3H), 4.71 (br, 2H), 5.04-5.21 (m, 4H), 6.79-7.25 (m, 6H), 7.34-7.52 (m, 16H), 7.65-7.87 (m, 1H), 8.32-8.49 (m, 1H); m/z, (ESI) 702 [C43H47N3O6+H]+.

Aufarbeitung

  1. temperatureheated to 55° C. for 75 h
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated under vacuum
  4. washeluting with 5-50% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-1636d5e5f75a4ebf8019bf4e16a1255f
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163758B2

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