Triphenylphosphine → HCID 66974094, compound

HRID 1396023Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([CH2:12][CH2:13][OH:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:15][C:16]1[CH:29]=[CH:28][C:19]([O:20][C:21]2[CH:22]=[C:23](O)[CH:24]=[CH:25][CH:26]=2)=[CH:18][CH:17]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([CH2:12][CH2:13][O:14][C:23]2[CH:24]=[CH:25][CH:26]=[C:21]([O:20][C:19]3[CH:18]=[CH:17][C:16]([Cl:15])=[CH:29][CH:28]=3)[CH:22]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution consisting of 3-(2-hydroxy-ethyl)-azetidine-1-carboxylic acid tert-butyl ester (4.39 g, 21.8 mmol), 3-(4-chloro-phenoxy)-phenol (4.81 g, 21.8 mmol) and THF (40 mL) was cooled at 0° C., treated with polymer supported triphenyl phosphine (10.9 g, 32.7 mmol) then diisopropyl azodicarboxylate (6.62 g, 32.7 mmol) dropwise over 30 min. After stirring for 15 min at 0° C., the reaction mixture was allowed to warm to room temperature and stirred for 16 h. The reaction mixture was filtered, the filtrate evaporated, and the residue purified (FCC) to give the title compound as a clear oil (6.39 g, 73%). MS (ESI+): calcd. for C22H26ClNO4, 403.16. m/z found, 426.2 (M+Na)+. 1H NMR (d6-DMSO): 7.43 (d, J=9.0 Hz, 2H), 7.28 (t, J=8.2 Hz, 1H), 7.03 (d, J=9.0 Hz, 2H), 6.72 (dd, J=8.3, 1.5 Hz, 1H), 6.59-6.55 (m, 2H), 3.98-3.84 (m, 4H), 3.59-3.50 (m, 2H), 2.70-2.58 (m, 1H), 2.02-1.89 (m, 2H), 1.36 (s, 9H).

Workup

additiontreated with polymer
temperatureto warm to room temperature
stirringstirred for 16 h
filtrationThe reaction mixture was filtered
customthe filtrate evaporated
customthe residue purified (FCC)

Sources & evidence

ORD record: ord-9af5a8e399cd4a86a1a878271036fa6a
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901111B2

Reaction notes

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