Potassium Carbonate → Methyl 3-[4-(azetidin-1-ylcarbonyl)-2-fluorophenoxy]-5-[(1S)-2-hydroxy-1-methylethoxy]benzoate

HRID 20505Notes

Reaction equation

[Si]([O:8][CH2:9][C@H:10]([CH3:23])[O:11][C:12]1[CH:13]=[C:14]([CH:19]=[C:20]([OH:22])[CH:21]=1)[C:15]([O:17][CH3:18])=[O:16])(C(C)(C)C)(C)C.[F:24][C:25]1[CH:26]=[C:27]([CH:34]=[CH:35][C:36]=1F)[C:28]([N:30]1[CH2:33][CH2:32][CH2:31]1)=[O:29].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[N:30]1([C:28]([C:27]2[CH:34]=[CH:35][C:36]([O:22][C:20]3[CH:19]=[C:14]([CH:13]=[C:12]([O:11][C@@H:10]([CH3:23])[CH2:9][OH:8])[CH:21]=3)[C:15]([O:17][CH3:18])=[O:16])=[C:25]([F:24])[CH:26]=2)=[O:29])[CH2:33][CH2:32][CH2:31]1

Participants

Conditions

Temperature: 160 °C

Procedure

To a portion of methyl 3-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)-5-hydroxybenzoate (102 mg, 0.3 mmol) and 1-(3,4-difluorobenzoyl)azetidine (71 mg, 0.36 mmol) in DMF (2.0 mL) was added potassium carbonate (207 mg, 1.5 mmol) and the stirred mixture heated at 160° C. in a ‘Smith Creator Microwave’ for 120 minutes. The mixture was allowed to reach ambient temperature and pressure then partitioned between ethyl acetate (2×25 mL) and water (25 mL). The organic layer was separated, washed with brine, dried (MgSO4), and evaporated in vacuo to give the crude product which was used without further purification (100 mg).

Workup

customto reach ambient temperature
custompressure then partitioned between ethyl acetate (2×25 mL) and water (25 mL)
customThe organic layer was separated
washwashed with brine
dry with materialdried (MgSO4)
customevaporated in vacuo

Sources & evidence

ORD record: ord-551d67b9c8754d62bbc83a72a7e5e48c
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07745475B2

Reaction notes

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