Methyl N-(triethylammoniosulfonyl)carbamate → 2-(4-Benzyloxy-3-ethyl-5-methyl-phenyl)-5-(4-isopropoxy-3-methyl-phenyl)-[1,3,4]oxadiazole

HRID 1666597Notes

Reaction equation

HRID 1666597 reaction equation
[CH:1]([O:4][C:5]1[CH:33]=[CH:32][C:8]([C:9]([NH:11][NH:12][C:13](=O)[C:14]2[CH:19]=[C:18]([CH3:20])[C:17]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[C:16]([CH2:29][CH3:30])[CH:15]=2)=[O:10])=[CH:7][C:6]=1[CH3:34])([CH3:3])[CH3:2].CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>C1COCC1.C(OCC)C>[CH2:22]([O:21][C:17]1[C:18]([CH3:20])=[CH:19][C:14]([C:13]2[O:10][C:9]([C:8]3[CH:32]=[CH:33][C:5]([O:4][CH:1]([CH3:3])[CH3:2])=[C:6]([CH3:34])[CH:7]=3)=[N:11][N:12]=2)=[CH:15][C:16]=1[CH2:29][CH3:30])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 674440334-benzyloxy-3-ethyl-5-methyl-benzoic acid N'-(4-isopropoxy-3-methyl-benzoyl)-hydrazide

Product 1

HCID 674468842-(4-Benzyloxy-3-ethyl-5-methyl-phenyl)-5-(4-isopropoxy-3-methyl-phenyl)-[1,3,4]oxadiazoleYield 83.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-benzyloxy-3-ethyl-5-methyl-benzoic acid N'-(4-isopropoxy-3-methyl-benzoyl)-hydrazide (1.57 g, 3.40 mmol) and Burgess reagent (1.06 g, 4.43 mmol) in THF (30 mL) is heated to 110° C. under microwave irradiation for 3 min. The mixture is cooled, diluted with diethyl ether, washed with water, dried over MgSO4, filtered and concentrated. The crude product is purified by CC on silica gel eluting with heptane:EA 5:1 to give 2-(4-benzyloxy-3-ethyl-5-methyl-phenyl)-5-(4-isopropoxy-3-methyl-phenyl)-[1,3,4]oxadiazole (1.25 g) as a colourless oil; LC-MS: tR=1.24 min, [M+1]+=443.58.

Workup

  1. temperatureThe mixture is cooled
  2. washwashed with water
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product is purified by CC on silica gel eluting with heptane:EA 5:1

Sources & evidence

ORD record
ord-ada131f5af7c4939a05a3d6d2ab721d7
Source dataset
uspto-grants-2011_10
Patent number
US08044076B2

Reaction notes

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