Toluene → HCID 178500718, compound

HRID 217246Notes

Reaction equation

HRID 217246 reaction equation
[CH3:1][O:2][C:3](=[O:10])[CH2:4][C@H:5]1[CH2:8][C@@H:7]([OH:9])[CH2:6]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N+:30]([C:33]1[CH:41]=[CH:40][C:36]([C:37](O)=[O:38])=[CH:35][CH:34]=1)([O-:32])=[O:31].C1(C)C=CC=CC=1>C1COCC1.N(C(OCC)=O)=NC(OCC)=O>[CH3:1][O:2][C:3]([CH2:4][C@H:5]1[CH2:8][C@H:7]([O:9][C:37](=[O:38])[C:36]2[CH:35]=[CH:34][C:33]([N+:30]([O-:32])=[O:31])=[CH:41][CH:40]=2)[CH2:6]1)=[O:10]

Participants

7

Reactant 4

HCID 1140TolueneHCID 61084-Nitrobenzoic AcidHCID 11776TriphenylphosphineHCID 178500715HCID 178500715, compound

Product 1

HCID 178500718HCID 178500718, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 220568ethyl N-ethoxycarbonyliminocarbamateSolvent

Procedure

To a solution of cis-(3-hydroxy-cyclobutyl)-acetic acid methyl ester (570 mg, 3.96 mmol), triphenylphosphine (2.08 g, 7.92 mmol), and 4-nitrobenzoic acid (1.32 g, 7.92 mmol) in dry THF (50 mL), 40% diethyl azodicarboxylate in toluene (1.42 mL, 7.92 mmol) is added at room temperature. The mixture is stirred at room temperature for 15 hours. The solvent is removed under reduced pressure, and the obtained residue is purified by silica gel column chromatography to give trans-4-nitro-benzoic acid 3-methoxycarbonylmethyl-cyclobutyl ester (558 mg, 48%); TLC (hexane/AcOEt, 3:1) Rf 0.31, 1H NMR (400 MHz, chloroform-d) δ ppm 2.28-2.35 (m, 2H), 2.44-2.51 (m, 2H), 2.56 (d, 2H), 2.82-2.87 (m, 1H), 3.69 (s, 3H), 5.33-5.40 (m, 1H). 8.18-8.30 (m, 4H).

Workup

  1. customThe solvent is removed under reduced pressure
  2. customthe obtained residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-bb7fbeaa7a0b487aa9a41ada6dc6f40d
Source dataset
uspto-grants-2012_06
Patent number
US08193349B2

Reaction notes

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