4-Hydroxybiphenyl → (2s,4r)-4-(n-Tert-butoxycarbonylglycylamino)-2-(4-biphenyloxy)methyl-n-tert-butoxycarbonylpyrrolidine

HRID 2185489Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2185489
N(C(OCC)=O)=NC(OCC)=O.[C:13]([O:17][C:18]([NH:20][CH2:21][C:22]([NH:24][C@H:25]1[CH2:29][N:28]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[C@H:27]([CH2:37][OH:38])[CH2:26]1)=[O:23])=[O:19])([CH3:16])([CH3:15])[CH3:14].[C:39]1([C:45]2[CH:50]=[CH:49][C:48](O)=[CH:47][CH:46]=2)[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[C:13]([O:17][C:18]([NH:20][CH2:21][C:22]([NH:24][C@H:25]1[CH2:29][N:28]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[C@H:27]([CH2:37][O:38][C:48]2[CH:49]=[CH:50][C:45]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)=[CH:46][CH:47]=2)[CH2:26]1)=[O:23])=[O:19])([CH3:15])([CH3:14])[CH3:16]

Komponenten

6

Edukt 4

HCID 71034-HydroxybiphenylHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 70172939(2s,4r)-4-(n-Tert-butoxycarbonylglycylamino)-2-hydroxymethyl-n-tert-butoxycarbonylpyrrolidine

Produkt 1

HCID 70177840(2s,4r)-4-(n-Tert-butoxycarbonylglycylamino)-2-(4-biphenyloxy)methyl-n-tert-butoxycarbonylpyrrolidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Diethyl azodicarboxylate (158 mL) was added to a mixture of (2S,4R)-4-(N-tert-butoxycarbonylglycylamino)-2-hydroxymethyl-N-tert-butoxycarbonylpyrrolidine (A, 310 mg), 4-phenylphenol (148 mg), and triphenyl phosphine (229 mg) in tetrahydrofuran (10 mL) under argon at room temperature. After stirring at room Ad temperature for 17 hr, the mixture was concentrated in vacuo to give a residue, which was purified by silica gel column chromatography (chloroform:methanol=200:1, v/v) to afford title compound (431 mg): 1H NMR (400 MHz, CDCl3) δ 1.44 (s, 18H), 2.01 (m, 1H), 2.38 (m, 1H), 3.21 (m, 1H), 3.72 (m, 1H), 3.77 (d, J=4.4 Hz, 2H), 3.99-4.25 (m, 3H), 4.68 (m, 1H), 5.49 (m, 1H), 6.85 (m, 1H), 6.97 (d, J=7.3 Hz, 2H), 7.29 (d, J=7.3 Hz, 1H), 7.40 (t, J=7.3 Hz, 2H), 7.48-7.63 (m, 4H).

Aufarbeitung

  1. concentrationthe mixture was concentrated in vacuo
  2. customto give a residue, which
  3. customwas purified by silica gel column chromatography (chloroform

Quellen und Nachweise

ORD-Eintrag
ord-dc96c9481e0a4ae9bdf7219629bd2253
Quelldatensatz
uspto-grants-2002_06
Patentnummer
US06399629B1

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