Iodine → Tert-butyl[2-(5-isopropyl-[1,3,4]oxadiazol-2-yl)-ethyl]-carbamate

HRID 1804564Notes

Reaction equation

HRID 1804564 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.II.C(N(CC)CC)C.[C:29]([NH:34][NH:35][C:36](=[O:47])[CH2:37][CH2:38][NH:39][C:40](=[O:46])[O:41][C:42]([CH3:45])([CH3:44])[CH3:43])(=O)[CH:30]([CH3:32])[CH3:31]>ClCCl>[CH:30]([C:29]1[O:47][C:36]([CH2:37][CH2:38][NH:39][C:40](=[O:46])[O:41][C:42]([CH3:43])([CH3:44])[CH3:45])=[N:35][N:34]=1)([CH3:31])[CH3:32]

Participants

6

Reactant 4

HCID 807IodineHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 57637099tert-butyl [3-(N'-isobutyryl-hydrazino)-3-oxo-propyl]-carbamate

Product 1

HCID 57637115Tert-butyl[2-(5-isopropyl-[1,3,4]oxadiazol-2-yl)-ethyl]-carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

20.00 g (43.00 mmol) PS-triphenylphosphine are placed in 240 ml dichloromethane, 10.88 g (42.87 mmol) iodine are added. The mixture is stirred for 0.1 hours at ambient temperature, then 12.10 ml (87.29 mmol) triethylamine are added dropwise. 5.83 g (21.33 mmol) tert-butyl [3-(N′-isobutyryl-hydrazino)-3-oxo-propyl]-carbamate dissolved in 150 ml dichloromethane are added. The reaction mixture is stirred for 24 hours at ambient temperature, then the precipitate is filtered off. The filtrate is evaporated down and purified by chromatography.

Workup

  1. additionare added
  2. stirringThe reaction mixture is stirred for 24 hours at ambient temperature
  3. filtrationthe precipitate is filtered off
  4. customThe filtrate is evaporated down
  5. custompurified by chromatography

Sources & evidence

ORD record
ord-9c605c0cd5cc4ea6adadedfa4294b203
Source dataset
uspto-grants-2013_01
Patent number
US08354418B2

Reaction notes

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