Ethanol → Ethyl 2-[3-[6-(azetidine-1-carbonyl)pyridin-3-yl]oxy-5-[(5-methylpyrazin-2-yl)carbamoyl]phenoxy]-4-hydroxy-butanoate

Reaction equation

[C:1](=[O:4])([O-])[O-:2].[K+].[K+].[N:7]1([C:11]([C:13]2[N:18]=[CH:17][C:16]([O:19][C:20]3[CH:21]=[C:22]([CH:33]=[C:34]([O:36][CH:37]4[CH2:41][CH2:40][O:39]C4=O)[CH:35]=3)[C:23]([NH:25][C:26]3[CH:31]=[N:30][C:29]([CH3:32])=[CH:28][N:27]=3)=[O:24])=[CH:15][CH:14]=2)=[O:12])[CH2:10][CH2:9][CH2:8]1.[CH2:43](O)[CH3:44]>>[N:7]1([C:11]([C:13]2[N:18]=[CH:17][C:16]([O:19][C:20]3[CH:35]=[C:34]([CH:33]=[C:22]([C:23](=[O:24])[NH:25][C:26]4[CH:31]=[N:30][C:29]([CH3:32])=[CH:28][N:27]=4)[CH:21]=3)[O:36][CH:37]([CH2:41][CH2:40][OH:39])[C:1]([O:2][CH2:43][CH3:44])=[O:4])=[CH:15][CH:14]=2)=[O:12])[CH2:8][CH2:9][CH2:10]1

Participants

Reactant 3

HCID 702Ethanol

HCID 11430Potassium Carbonate

HCID 597611403-[6-(azetidine-1-carbonyl)pyridin-3-yl]oxy-N-(5-methylpyrazin-2-yl)-5-(2-oxooxolan-3-yl)oxy-benzamide2×

Product 1

HCID 59761144Ethyl 2-[3-[6-(azetidine-1-carbonyl)pyridin-3-yl]oxy-5-[(5-methylpyrazin-2-yl)carbamoyl]phenoxy]-4-hydroxy-butanoate

Procedure

Potassium carbonate (113 mg, 0.82 mmol) was added to a solution of 3-[6-(azetidine-1-carbonyl)pyridin-3-yl]oxy-N-(5-methylpyrazin-2-yl)-5-(2-oxooxolan-3-yl)oxy-benzamide (Intermediate 29) (800 mg, 1.6 mmol) in ethanol (80 mL) at 0° C. under nitrogen. The reaction was allowed to warm to RT and stirred for 4 hours. The reaction mixture was filtered through silica, washing well with ethyl acetate, and concentrated to afford crude product which was used directly in the next stage without further purification.