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Ethyl Acetate → (R)-methyl 4-(phenylthio)-3-(4-sulfamoyl-2-(trifluoromethylsulfonyl)phenylamino)butanoate

HRID 1771162
Notes
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Reaction equation

HRID 1771162 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:4][C:3]=1[S:12]([C:15]([F:18])([F:17])[F:16])(=[O:14])=[O:13].CC[N:21]([CH:25]([CH3:27])[CH3:26])C(C)C.[C:28]([O:31][CH2:32]C)(=[O:30])C>CN(C=O)C>[C:5]1([S:8][CH2:27][C@H:25]([NH:21][C:2]2[CH:7]=[CH:6][C:5]([S:8](=[O:10])(=[O:9])[NH2:11])=[CH:4][C:3]=2[S:12]([C:15]([F:18])([F:17])[F:16])(=[O:14])=[O:13])[CH2:26][C:28]([O:31][CH3:32])=[O:30])[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 250584524-Fluoro-3-((trifluoromethyl)sulfonyl)benzenesulfonamide2×

Product 1

HCID 66723774(R)-methyl 4-(phenylthio)-3-(4-sulfamoyl-2-(trifluoromethylsulfonyl)phenylamino)butanoateYield 56%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
50 °C

Procedure

4-Fluoro-3-(trifluoromethylsulfonyl)benzenesulfonamide (INTERMEDIATE 6, 21.67 g, 71.22 mmol) and DIPEA (129 ml, 738 mmol) were added to a solution of (R)-methyl 3-amino-4-(phenylthio)butanoate, trifluoroacetic acid salt (INTERMEDIATE 7, STEP 2) in DMF (20 ml). The resulting reaction mixture was heated at 50° C. for 1.5 hours, allowed to cool to room temperature, diluted with ethyl acetate (500 ml), and washed with water (250 ml) and brine (250 ml). The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. The concentrate was purified by column chromatography (ISCO, eluting with 0→30% EtOAc/DCM over 54 minutes) to give the title product (20.5 g, yield: 56%).

Workup

  1. customThe resulting reaction mixture
  2. temperatureto cool to room temperature
  3. washwashed with water (250 ml) and brine (250 ml)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe concentrate was purified by column chromatography (ISCO, eluting with 0→30% EtOAc/DCM over 54 minutes)

Sources & evidence

ORD record
ord-243dbb3a4f1443dca3877ae081085f46
Source dataset
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09248140B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes