Tert-butyl 4-((2-cyanoadamantan-2-yl)methoxy)-5-cyclopropyl-2-fluorobenzoate → 5-Cyclopropyl-2-fluoro-4-((1-fluorocyclohexyl)methoxy)benzoic acid

HRID 1849797Notes

Reaction equation

HRID 1849797 reaction equation
C(C1(COC2C(C3CC3)=CC(C(OC(C)(C)C)=O)=C(F)C=2)C2CC3CC(CC1C3)C2)#N.[CH:32]1([C:35]2[C:36]([O:49][CH2:50][C:51]3([F:57])[CH2:56][CH2:55][CH2:54][CH2:53][CH2:52]3)=[CH:37][C:38]([F:48])=[C:39]([CH:47]=2)[C:40]([O:42]C(C)(C)C)=[O:41])[CH2:34][CH2:33]1>>[CH:32]1([C:35]2[C:36]([O:49][CH2:50][C:51]3([F:57])[CH2:56][CH2:55][CH2:54][CH2:53][CH2:52]3)=[CH:37][C:38]([F:48])=[C:39]([CH:47]=2)[C:40]([OH:42])=[O:41])[CH2:34][CH2:33]1

Participants

3

Reactant 2

HCID 86703654Tert-butyl 4-((2-cyanoadamantan-2-yl)methoxy)-5-cyclopropyl-2-fluorobenzoateHCID 86703679Tert-butyl 5-cyclopropyl-2-fluoro-4-((1-fluorocyclohexyl)-methoxy)benzoate

Product 1

HCID 867036815-Cyclopropyl-2-fluoro-4-((1-fluorocyclohexyl)methoxy)benzoic acid

Procedure

Following the procedure as described in Example 332 Step 6 and making non-critical variations to replace tert-butyl 4-((2-cyanoadamantan-2-yl)methoxy)-5-cyclopropyl-2-fluorobenzoate with tert-butyl 5-cyclopropyl-2-fluoro-4-((1-fluorocyclohexyl)-methoxy)benzoate, the title compound was obtained as a colorless solid (0.48 g, 80%): 1H NMR (300 MHz, CDCl3) δ 7.52 (d, J=8.4 Hz, 1H), 6.57 (d, J=12.5 Hz, 1H), 3.98 (d, J=17.9 Hz, 2H), 2.10-1.89 (m, 2H), 1.76-1.51 (m, 6H), 1.39-1.21 (m, 1H), 0.95-0.86 (m, 2H), 0.69-0.59 (m, 2H).

Sources & evidence

ORD record
ord-584765a55f5d425680df31d272e4e67b
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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