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Hydrochloric Acid → 8-(5-Methyl-2-phenyl-oxazol-4-yl)-2-[1,2,3]triazol-2-yl-oct-4-ynoic acid ethyl ester

HRID 2121702
Notes
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Reaction equation

HRID 2121702 reaction equation
CC(C)([O-])C.[K+].[CH2:7]([O:9][C:10](=[O:17])[CH2:11][N:12]1[N:16]=[CH:15][CH:14]=[N:13]1)[CH3:8].Br[CH2:19][C:20]#[C:21][CH2:22][CH2:23][CH2:24][C:25]1[N:26]=[C:27]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[O:28][C:29]=1[CH3:30].Cl>C1COCC1.CCOC(C)=O>[CH2:7]([O:9][C:10](=[O:17])[CH:11]([N:12]1[N:13]=[CH:14][CH:15]=[N:16]1)[CH2:19][C:20]#[C:21][CH2:22][CH2:23][CH2:24][C:25]1[N:26]=[C:27]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[O:28][C:29]=1[CH3:30])[CH3:8]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10329488Ethyl 2-(2H-1,2,3-triazol-2-YL)acetateHCID 120932704-(6-Bromo-hex-4-ynyl)-5-methyl-2-phenyl-oxazoleHCID 23665647Potassium tert-butoxide

Product 1

HCID 120932758-(5-Methyl-2-phenyl-oxazol-4-yl)-2-[1,2,3]triazol-2-yl-oct-4-ynoic acid ethyl esterYield 60.9%

Reagents, catalysts & solvents

2
HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Potassium t-butoxide (2.6 mL, 2.6 mmol) was added to a to a solution of [1,2,3]triazol-2-yl-acetic acid ethyl ester (355 mg, 2.3 mmol) in THF (30 mL) at −78° C. under N2 atmosphere and stirred for 1 hour. A solution of bromide 1-9 (1.5 g, 4.5 mmol) in THF (30 mL) was then added and the solution allowed to equilibrate to 0° C. for 1 hour. Reaction was then poured into dilute aqueous HCl and diluted with EtOAc. The organic layer was washed with water, brine, and dried over MgSO4. Chromatography with 20% EtOAc/Hex gave 550 mg of a mixture of mono-1-4 and bis-alkylated products. The mixture was not separated, and was taken on to hydrolysis step.

Workup

  1. waitto equilibrate to 0° C. for 1 hour
  2. customReaction
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-9b4b219963b8473cb2481dedf1a8bbc4
Source dataset
uspto-grants-2004_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06696474B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes