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Methanol → (R)-3-acetyl-5-((1-phenylethyl)carbamoyl)benzoic acid

HRID 1454206
Notes
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Reaction equation

HRID 1454206 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:11]=[C:12]([C:14](=[O:24])[NH:15][C@@H:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH3:17])[CH:13]=1)[C:7]([O:9]C)=[O:8])(=[O:3])[CH3:2].CO.O.[Li+].[OH-]>C1COCC1>[C:1]([C:4]1[CH:5]=[C:6]([CH:11]=[C:12]([C:14](=[O:24])[NH:15][C@@H:16]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH3:17])[CH:13]=1)[C:7]([OH:9])=[O:8])(=[O:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 3939Lithium HydroxideHCID 57529287(R)-methyl 3-acetyl-5-((1-phenylethyl)-carbamoyl)benzoate

Product 1

HCID 57529301(R)-3-acetyl-5-((1-phenylethyl)carbamoyl)benzoic acidYield 95%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

To a solution of (R)-methyl 3-acetyl-5-((1-phenylethyl)-carbamoyl)benzoate (332 mg, 1.02 mmol) in a mixture of THF (1.4 mL), MeOH (2.8 mL) and H2O (7.0 mL), was added LiOH (73.4 mg, 3.06 mmol) and the mixture was stirred at room temperature for 1 h. The mixture was concentrated and partitioned between ethyl acetate and H2O. The aqueous layer was washed with ethyl acetate twice and acidified with 1N HCl solution to pH around 2˜3. The aqueous layer was extracted with ethyl acetate 3 times and the combined organic layers were dried over sodium sulfate and concentrated under vacuum to give the title compound which was ready for next step without further purification (300 mg, 95% yield): HPLC retention time: 1.662 min (method A). MS (ESI) (M+H)+ 311.00.

Workup

  1. concentrationThe mixture was concentrated
  2. custompartitioned between ethyl acetate and H2O
  3. washThe aqueous layer was washed with ethyl acetate twice
  4. extractionThe aqueous layer was extracted with ethyl acetate 3 times
  5. dry with materialthe combined organic layers were dried over sodium sulfate
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-852e808982134483b8091e66885b6695
Source dataset
uspto-grants-2009_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07476764B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes