4-Cyanobenzoic acid → HCID 67111403, compound

HRID 1365102Notes

Reaction equation

HRID 1365102 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][CH:4]=1)#[N:2].[NH2:12][C@H:13]([CH2:18]O)[C:14]([CH3:17])([CH3:16])[CH3:15]>ClC1C=CC=CC=1>[C:14]([C@H:13]1[CH2:18][O:9][C:7]([C:6]2[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:11][CH:10]=2)=[N:12]1)([CH3:17])([CH3:16])[CH3:15]

Participants

4

Reactant 2

HCID 120874-Cyanobenzoic acidHCID 2734079(2S)-2-Amino-3,3-dimethyl-1-butanol

Product 1

HCID 67111403HCID 67111403, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

Under an argon atmosphere, a mixture of 4-cyanobenzoic acid (7.2 mmol), L-tert-leucinol (6.0 mmol), Zn4(OCOCF3)6O (0.3 mmol) and chlorobenzene (10 mL) was heated under reflux for 18 hours. From the resulting solution, the solvent was removed using an evaporator, and the residues were purified by silica gel column chromatography (hexane/ethyl acetate=10/1 (V/V)) to give (S)-4-tert-butyl-2-(4-cyanophenyl)-1,3-oxazoline in 78% yield.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 18 hours
  3. customFrom the resulting solution, the solvent was removed
  4. customan evaporator
  5. customthe residues were purified by silica gel column chromatography (hexane/ethyl acetate=10/1 (V/V))

Sources & evidence

ORD record
ord-627bd3a051d245af89ca6029f92870f1
Source dataset
uspto-grants-2011_02
Patent number
US07888513B2

Reaction notes

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