4-Nitrobenzoic Acid → HCID 121396359, compound

HRID 60698Notes

Reaction equation

[CH3:1][C:2]1([CH3:14])[O:6][C@H:5]2[O:7][C@H:8]([C@H:10]([OH:13])[CH2:11][CH3:12])[CH2:9][C@H:4]2[O:3]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N+:34]([C:37]1[CH:45]=[CH:44][C:40]([C:41](O)=[O:42])=[CH:39][CH:38]=1)([O-:36])=[O:35].N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[N+:34]([C:37]1[CH:38]=[CH:39][C:40]([C:41]([O:13][C@H:10]([C@H:8]2[O:7][C@@H:5]3[O:6][C:2]([CH3:1])([CH3:14])[O:3][C@@H:4]3[CH2:9]2)[CH2:11][CH3:12])=[O:42])=[CH:44][CH:45]=1)([O-:36])=[O:35]

Participants

Conditions

Temperature: 18 °C

Procedure

To a stirred solution of (1R)-1-[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]propan-1-ol (compound 6c, 50 g, 245 mmol), triphenylphosphine (195 g, 743 mmol), 4-nitrobenzoic acid (124 g, 743 mmol) in THF (1200 mL) was added diethyl azodicarboxylate (130 g, 743 mmol) dropwise at 0° C. under N2. After being stirred at 18° C. for 10 hours, the mixture was quenched by addition of saturated NaHCO3 solution and extracted with EtOAc. The organic layers were combined, dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography on silica gel (eluting with 1:3 EtOAc in petroleum ether) to afford 61 g of [(1S)-1-[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]propyl] 4-nitrobenzoate (compound 6d) as a slight yellow solid.

Workup

customthe mixture was quenched by addition of saturated NaHCO3 solution
extractionextracted with EtOAc
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
customThe residue was purified by column chromatography on silica gel (eluting with 1:3 EtOAc in petroleum ether)

Sources & evidence

ORD record: ord-08163273cf64431593e3ec59ae2814aa
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09441008B2

Reaction notes

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