Water → (S)-t-Butyl 2-(5-((3,4-dimethoxyphenoxy)methyl)-1,3,4-oxadiazol-2-yl)pyrrolidine-1-carboxylate

HRID 710040Notes

Reaction equation

HRID 710040 reaction equation
[C:1]1(C)C=CC=CC=1.CO[C:10]1[CH:11]=[C:12]([CH:33]=[CH:34][C:35]=1[O:36][CH3:37])[O:13][CH2:14][C:15]([NH:17][NH:18][C:19]([C@@H:21]1[CH2:25][CH2:24][CH2:23][N:22]1[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=O)=[O:16].CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC.[OH2:53]>>[CH3:1][O:53][C:34]1[CH:33]=[C:12]([CH:11]=[CH:10][C:35]=1[O:36][CH3:37])[O:13][CH2:14][C:15]1[O:16][C:19]([C@@H:21]2[CH2:25][CH2:24][CH2:23][N:22]2[C:26]([O:28][C:29]([CH3:30])([CH3:31])[CH3:32])=[O:27])=[N:18][N:17]=1

Participants

5

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 86706750(S)-t-Butyl 2-(2-(2-(3,4-dimethoxyphenoxy)acetyl)hydrazinecarbonyl)pyrrolidine-1-carboxylate

Product 1

HCID 86706751(S)-t-Butyl 2-(5-((3,4-dimethoxyphenoxy)methyl)-1,3,4-oxadiazol-2-yl)pyrrolidine-1-carboxylate

Conditions

Temperature
120 °C

Procedure

To a toluene (700 ml) solution of the compound (61.0 g) obtained in Example 8-(1), Burgess reagent (45.0 g) was added and the mixture was stirred at 120° C. for 4 hours. After adding water to the reaction mixture, the organic layer extracted with AcOEt was dried (Na2SO4), filtered and had the solvent distilled off under reduced pressure; the resulting residue was purified by silica gel chromatography (AcOEt) to give the titled compound (42.0 g).

Workup

  1. extractionthe organic layer extracted with AcOEt
  2. dry with materialwas dried (Na2SO4)
  3. filtrationfiltered
  4. distillationdistilled off under reduced pressure
  5. customthe resulting residue was purified by silica gel chromatography (AcOEt)

Sources & evidence

ORD record
ord-8423abb2aff74002af90e491844988b4
Source dataset
uspto-grants-2015_11
Patent number
US09181229B2

Reaction notes

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