HCID 86703589, compound → HCID 86703593, compound

HRID 1849718Notes

Reaction equation

[C@@H:1]12[CH2:7][C@@H:4]([CH2:5][CH2:6]1)[CH2:3][C@@H:2]2[O:8][C:9]1[C:21]([CH:22]2[CH2:24][CH2:23]2)=[CH:20][C:12]([C:13]([O:15]C(C)(C)C)=[O:14])=[C:11]([F:25])[CH:10]=1.[C@@H]12C[C@@H](CC1)C[C@H]2OC1C(C2CC2)=CC(C(OC(C)(C)C)=O)=C(F)C=1>>[C@@H:1]12[CH2:7][C@@H:4]([CH2:5][CH2:6]1)[CH2:3][C@H:2]2[O:8][C:9]1[C:21]([CH:22]2[CH2:24][CH2:23]2)=[CH:20][C:12]([C:13]([OH:15])=[O:14])=[C:11]([F:25])[CH:10]=1

Participants

Reactant 2

HCID 86703589HCID 86703589, compound

HCID 86703594HCID 86703594, compound

Product 1

HCID 86703593HCID 86703593, compoundYield 57%

Procedure

Following the procedure as described in Example 283 step 3 and making variations as required to replace tert-butyl 4-((1S,2S,4R)-bicyclo[2.2.1]heptan-2-yloxy)-5-cyclopropyl-2-fluorobenzoate with tert-butyl 4-((1S,2R,4R)-bicyclo[2.2.1]heptan-2-yloxy)-5-cyclopropyl-2-fluorobenzoate. Purification by silica gel column chromatography (2:1 hexanes:ethyl acetate (+0.2% acetic acid v/v)) gave the title compound as a colorless solid (0.50 g, 57%): 1H NMR (300 MHz, DMSO-d6) δ 12.76 (br s, 1H), 7.27 (d, J=8.5 Hz, 1H), 6.76 (d, J=13.2 Hz, 1H), 4.80-4.70 (m, 1H), 2.59-2.52 (m, 1H), 2.25-2.18 (m, 1H), 2.15-2.03 (m, 1H), 2.02-1.79 (m, 2H), 1.61-1.48 (m, 1H), 1.45-1.17 (m, 4H), 0.97-0.82 (m, 3H), 0.60-0.50 (m, 2H); MS (ES+) m/z 291.1 (M+1).

Workup

customPurification by silica gel column chromatography (2:1 hexanes

Sources & evidence

ORD record: ord-ce24b11097274a4fa0609469c0103617
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952169B2

Reaction notes

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