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

HRID 2185489Notes

Reaction equation

HRID 2185489 reaction equation
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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-dc96c9481e0a4ae9bdf7219629bd2253
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

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