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Sodium Hydroxide → HCID 59063643, compound

HRID 413314
Notes
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Reaction equation

HRID 413314 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]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 59063640HCID 59063640, compound

Product 1

HCID 59063643HCID 59063643, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

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

  1. extractionThe aqueous phase was extracted with four portions of methylene chloride
  2. dry with materialthe combined organic extracts were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. 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
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06566377B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes