4-Nitrobenzoic Acid → HCID 178525740, compound

HRID 2235192Notes

Reaction equation

[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([N:8]2[CH2:12][CH2:11][CH2:10][C:9]2=[O:13])[CH2:4][CH2:3]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N+:33]([C:36]1[CH:44]=[CH:43][C:39]([C:40](O)=[O:41])=[CH:38][CH:37]=1)([O-:35])=[O:34].N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[O:13]=[C:9]1[CH2:10][CH2:11][CH2:12][N:8]1[C@@H:5]1[CH2:4][CH2:3][C@H:2]([O:1][C:40](=[O:41])[C:39]2[CH:38]=[CH:37][C:36]([N+:33]([O-:35])=[O:34])=[CH:44][CH:43]=2)[CH2:7][CH2:6]1

Participants

Conditions

Temperature: -5 °C

Procedure

Dissolve 1-(trans-4-hydroxy-cyclohexyl)-pyrrolidin-2-one (Preparation 14) (144 g; 0.79 mol) in dry tetrahydrofuran (5 L) and cool to −5° C. under nitrogen. Add triphenylphosphine (310 g; 1.185 mol) and 4-nitrobenzoic acid (198 g; 1.185 mol). Add diisopropyl azodicarboxylate (230 mL; 1.185 mol) drop-wise and stir at room temperature overnight. Add saturated aqueous sodium hydrogencarbonate (1 L) extract into dichloromethane (2×2.5 L) in a 20 L separating funnel. Dry the combined organic layers over magnesium sulfate, filter and concentrate. Purify over silica gel (iso-hexane/ethyl acetate 50-100% then 10% methanol in ethyl acetate) to afford 163 g (62%) of the title compound.

Workup

extractionAdd saturated aqueous sodium hydrogencarbonate (1 L) extract into dichloromethane (2×2.5 L) in a 20 L
customseparating funnel
dry with materialDry the combined organic layers over magnesium sulfate
filtrationfilter
concentrationconcentrate
customPurify over silica gel (iso-hexane/ethyl acetate 50-100%

Sources & evidence

ORD record: ord-4ba6344735b64a2d8b78021efb151fb9
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07713979B2

Reaction notes

Loading…