Sodium Hydroxide → HCID 59063643, compound
Reaction equation
[OH:1][C@H:2]([C:20]1[CH:21]=[CH:22][C:23]([NH:26]C(=O)C)=[N:24][CH:25]=1)[CH2:3][NH:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:15]=[C:16]([CH3:19])[S:17][CH:18]=2)=[CH:10][CH:9]=1.[OH-].[Na+]>C(O)C.O>[NH2:26][C:23]1[N:24]=[CH:25][C:20]([C@@H:2]([OH:1])[CH2:3][NH:4][CH2:5][CH2:6][O:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]3[N:15]=[C:16]([CH3:19])[S:17][CH:18]=3)=[CH:10][CH:9]=2)=[CH:21][CH:22]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
In a round-bottomed flask, (R)-N-[5-(1-hydroxy-2-{2-[4-(2-methyl-thiazol-4-yl)-phenoxy]-ethylamino}-ethyl)-pyridin-2-yl]-acetamide (74 mg, 0.18 mmol) was dissolved in 1.0 mL of ethanol, and 1.0 mL of 2 M sodium hydroxide was added to the solution. The reaction mixture was then heated to about 80° C. for about twenty minutes, and was then diluted with water and adjusted to about pH 11. The aqueous phase was extracted with four portions of methylene chloride, and the combined organic extracts were dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting crude material was purified by column chromatography (methylene chloride to 20% methanol/methylene chloride) to afford 49 mg (74%) of the desired product. LRMS ([M+1]+): 371.2.
Workup
- extractionThe aqueous phase was extracted with four portions of methylene chloride
- dry with materialthe combined organic extracts were dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe resulting crude material was purified by column chromatography (methylene chloride to 20% methanol/methylene chloride)
Sources & evidence
- ORD record
- ord-b00d736c87a04941a0e24352e1ec7cfe
- Source dataset
- uspto-grants-2003_05
- Patent number
- US06566377B2
Reaction notes
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