Tert-butyl 4-((2-cyanoadamantan-2-yl)methoxy)-5-cyclopropyl-2-fluorobenzoate → 5-Cyclopropyl-4-((4,4-difluorocyclohexyl)oxy)-2-fluorobenzoic acid

HRID 1849824Notes

Reaction equation

HRID 1849824 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:46][CH:47]3[CH2:52][CH2:51][C:50]([F:54])([F:53])[CH2:49][CH2:48]3)=[CH:37][C:38]([F:45])=[C:39]([CH:44]=2)[C:40]([O:42]C)=[O:41])[CH2:34][CH2:33]1>>[CH:32]1([C:35]2[C:36]([O:46][CH:47]3[CH2:52][CH2:51][C:50]([F:54])([F:53])[CH2:49][CH2:48]3)=[CH:37][C:38]([F:45])=[C:39]([CH:44]=2)[C:40]([OH:42])=[O:41])[CH2:33][CH2:34]1

Participants

3

Reactant 2

HCID 86703654Tert-butyl 4-((2-cyanoadamantan-2-yl)methoxy)-5-cyclopropyl-2-fluorobenzoateHCID 86703711Methyl 5-cyclopropyl-4-((4,4-difluorocyclohexyl)oxy)-2-fluorobenzoate

Product 1

HCID 867037125-Cyclopropyl-4-((4,4-difluorocyclohexyl)oxy)-2-fluorobenzoic acid

Procedure

Following the procedure as described in Example 332 Step 6, and making variations as required to replace tert-butyl 4-((2-cyanoadamantan-2-yl)methoxy)-5-cyclopropyl-2-fluorobenzoate with methyl 5-cyclopropyl-4-((4,4-difluorocyclohexyl)oxy)-2-fluorobenzoate, the title compound was obtained as a colorless solid (0.32 g, quant. yield): 1H NMR (300 MHz, CDCl3) δ 7.54 (d, J=8.4 Hz, 1H), 6.58 (d, J=12.7 Hz, 1H), 4.60 (br s, 1H), 2.20-1.92 (m, 9H), 0.94-0.88 (m, 2H), 0.65-0.60 (m, 2H); MS (ES−) m/z 313.2 (M−1).

Sources & evidence

ORD record
ord-28ccc5a2af884666809f07e437e760c9
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

Loading…