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

HRID 2185489노트

반응식

HRID 2185489 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-dc96c9481e0a4ae9bdf7219629bd2253
출처 데이터셋
uspto-grants-2002_06
특허 번호
US06399629B1

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