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Lawesson's reagent → (S)-t-Butyl 2-(5-((3,4-dimethoxyphenoxy)methyl)-1,3,4-thiadiazol-2-yl)pyrrolidine-1-carboxylate

HRID 710058
Notes
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Reaction equation

HRID 710058 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:26]=[CH:27][C:28]=1[O:29][CH3:30])[O:6][CH2:7][C:8]([NH:10][NH:11][C:12]([C@@H:14]1[CH2:18][CH2:17][CH2:16][N:15]1[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=O)=O.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:40])=CC=1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:26]=[CH:27][C:28]=1[O:29][CH3:30])[O:6][CH2:7][C:8]1[S:40][C:12]([C@@H:14]2[CH2:18][CH2:17][CH2:16][N:15]2[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[N:11][N:10]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 86706750(S)-t-Butyl 2-(2-(2-(3,4-dimethoxyphenoxy)acetyl)hydrazinecarbonyl)pyrrolidine-1-carboxylate

Product 1

HCID 86706771(S)-t-Butyl 2-(5-((3,4-dimethoxyphenoxy)methyl)-1,3,4-thiadiazol-2-yl)pyrrolidine-1-carboxylateYield 54.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

To a toluene (30 ml) solution of the compound (540 mg) obtained in Example 8-(1), Lawesson's reagent (750 mg) was added and the mixture was stirred at 90° C. for 6 hours. After adding water, extraction was conducted with AcOEt. The solvent was distilled off under reduced pressure and the residue was purified by silica gel chromatography (AcOEt/hexane) to give the titled compound (291 mg).

Workup

  1. additionAfter adding
  2. extractionwater, extraction
  3. distillationThe solvent was distilled off under reduced pressure
  4. customthe residue was purified by silica gel chromatography (AcOEt/hexane)

Sources & evidence

ORD record
ord-d87a05b49c254b14b001469273645b3a
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09181229B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes