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Hydrochloric Acid → Methyl {4-[4-(tert.-butoxy)-4-oxo-n-butyl]-3-(4-chlorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl}-acetate

HRID 660898
Notes
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Reaction equation

HRID 660898 reaction equation
[CH3:1][O:2][C:3](=[O:18])[CH2:4][N:5]1[C:9](=[O:10])[NH:8][C:7]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)=[N:6]1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.Br[CH2:30][CH2:31][CH2:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34].Cl>CN(C=O)C.COCCOC>[C:36]([O:35][C:33](=[O:34])[CH2:32][CH2:31][CH2:30][N:8]1[C:9](=[O:10])[N:5]([CH2:4][C:3]([O:2][CH3:1])=[O:18])[N:6]=[C:7]1[C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)([CH3:39])([CH3:38])[CH3:37]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 2733832Lithium hexamethyldisilazaneHCID 2757253tert-Butyl 4-bromobutanoateHCID 136199105Methyl[3-(4-chlorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-acetate

Product 1

HCID 58011851Methyl {4-[4-(tert.-butoxy)-4-oxo-n-butyl]-3-(4-chlorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl}-acetate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
70 °C

Procedure

Under an argon atmosphere, a solution of 130 mg (0.38 mmol) of the compound from Example 222A in 1 ml DMF and 2 ml DME at 0° C. is treated with 505 μl of an LiHMDS solution (1 M in THF, 505 μmol). The cooling bath is removed and the mixture stirred for 15 mins at RT before addition of 113 mg (505 μmol) of tert.-butyl 4-bromobutanoate. The mixture is stirred overnight at 70° C. After cooling, 0.5 ml of 1 N hydrochloric acid are added. The reaction mixture is then directly separated by preparative HPLC (Method 20). 48 mg (30% of theory) of the title compound are obtained.

Workup

  1. customThe cooling bath is removed
  2. temperatureAfter cooling
  3. customThe reaction mixture is then directly separated by preparative HPLC (Method 20)

Sources & evidence

ORD record
ord-8360cfc82d2b4e2583cd03687fa090ef
Source dataset
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08084481B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes