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Dimethylformamide → t-butyl (1S)-2-(3-fluorophenoxy)-1-methylethylcarbamate

HRID 12406
Notes
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Reaction equation

HRID 12406 reaction equation
Cl[CH2:2][C@@H:3]([NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[CH3:4].[F:13][C:14]1[CH:15]=[C:16]([OH:20])[CH:17]=[CH:18][CH:19]=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>C(OCC)(=O)C>[F:13][C:14]1[CH:15]=[C:16]([CH:17]=[CH:18][CH:19]=1)[O:20][CH2:2][C@@H:3]([NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[CH3:4]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 97433-FluorophenolHCID 11430Potassium CarbonateHCID 86761117t-butyl (1S)-2-chloro-1-methylethylcarbamate

Product 1

HCID 86761118t-butyl (1S)-2-(3-fluorophenoxy)-1-methylethylcarbamate

Reagents, catalysts & solvents 1

HCID 8857
Ethyl Acetate
Solvent

Conditions

Temperature
95 °C

Procedure

To the compound (500 mg) obtained in Step 3 were added 3-fluorophenol (84 μl), potassium carbonate (250 mg) and DMF (2 ml), and the mixture was stirred overnight at 95° C. The reaction mixture was diluted with ethyl acetate. After washing with water, the organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated to give the title compound as a crude product.

Workup

  1. washAfter washing with water
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated

Sources & evidence

ORD record
ord-b140c6747a1a44558eefb386d2991521
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07728005B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes