Pyrrolidine → HCID 67119126, compound

HRID 2076643Notes

Reaction equation

N1CCCC1.C(OC([O:13][C:14]1[C:26]([C:27]([F:30])([F:29])[F:28])=[CH:25][CH:24]=[C:23]([CH2:31][O:32][C:33]2[CH:38]=[CH:37][C:36]([C:39]3[CH:44]=[CH:43][CH:42]=[C:41]([CH2:45][C:46]([O:48][CH3:49])=[O:47])[C:40]=3[CH3:50])=[CH:35][CH:34]=2)[C:15]=1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=O)(C)(C)C>O1CCCC1>[OH:13][C:14]1[C:26]([C:27]([F:29])([F:30])[F:28])=[CH:25][CH:24]=[C:23]([CH2:31][O:32][C:33]2[CH:38]=[CH:37][C:36]([C:39]3[CH:44]=[CH:43][CH:42]=[C:41]([CH2:45][C:46]([O:48][CH3:49])=[O:47])[C:40]=3[CH3:50])=[CH:35][CH:34]=2)[C:15]=1[C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17]

Participants

Conditions

Temperature: 40 °C

Procedure

Pyrrolidine (3 μl, 0.036 mmol) was added to a solution of tert-butyl 2-[(tert-butoxycarbonyl)oxy]-6-[({3′-[(methoxycarbonyl)methyl]-2′-methyl-1,1′-biphenyl-4-yl}oxy)methyl]-3-(trifluoromethyl)benzoate (19 mg, 0.030 mmol) obtained in Example (33-4) in tetrahydrofuran (1 ml), and the mixture was stirred at 40° C. for 1 hour. The residue obtained by removing the solvent under reduced pressure was purified by silica gel preparative thin layer chromatography (developing solvent: n-hexane/ethyl acetate=3/1) to give tert-butyl 2-hydroxy-6-[({3′-[(methoxycarbonyl)methyl]-2′-methyl-1,1′-biphenyl-4-yl}oxy)methyl]-3-(trifluoromethyl)benzoate as a colorless oil (16 mg, yield: 100%).

Workup

customThe residue obtained
customby removing the solvent under reduced pressure
customwas purified by silica gel preparative thin layer chromatography (developing solvent: n-hexane/ethyl acetate=3/1)

Sources & evidence

ORD record: ord-81e42b5bb500492db874d9349fe11187
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07923573B2

Reaction notes

Loading…