HCID 86703589, compound → HCID 86703599, compound

HRID 1849724Notes

Reaction equation

[C@@H]12C[C@@H](CC1)C[C@@H]2OC1C(C2CC2)=CC(C(OC(C)(C)C)=O)=C(F)C=1.[C:26]12([CH2:36][O:37][C:38]3[C:50]([CH:51]4[CH2:53][C:52]4([F:55])[F:54])=[CH:49][C:41]([C:42]([O:44]C(C)(C)C)=[O:43])=[C:40]([F:56])[CH:39]=3)[CH2:35][CH:30]3[CH2:31][CH:32]([CH2:34][CH:28]([CH2:29]3)[CH2:27]1)[CH2:33]2>>[C:26]12([CH2:36][O:37][C:38]3[C:50]([CH:51]4[CH2:53][C:52]4([F:54])[F:55])=[CH:49][C:41]([C:42]([OH:44])=[O:43])=[C:40]([F:56])[CH:39]=3)[CH2:35][CH:30]3[CH2:29][CH:28]([CH2:34][CH:32]([CH2:31]3)[CH2:33]1)[CH2:27]2

Participants

Reactant 2

HCID 86703589HCID 86703589, compound

HCID 86703600HCID 86703600, compound

Product 1

HCID 86703599HCID 86703599, compoundYield 54%

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-(adamantan-1-ylmethoxy)-5-(2,2-difluorocyclopropyl)-2-fluorobenzoate. Purification by trituration with methanol gave the title compound as a colorless solid (0.45 g, 54%): 1H NMR (300 MHz, DMSO-d6) δ 12.91 (br s, 1H), 7.58 (d, J=8.6 Hz, 1H), 6.94 (d, J=12.7 Hz, 1H), 3.68-3.56 (m, 2H), 2.84-2.70 (m, 1H), 1.99-1.90 (m, 4H), 1.89-1.78 (m, 1H), 1.71-1.56 (m, 12H); MS (ES+) m/z 381.2 (M+1).

Workup

customPurification by trituration with methanol

Sources & evidence

ORD record: ord-23662394b4bc484f8779426d0562b6d8
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952169B2

Reaction notes

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