Hydrochloric Acid → HCID 178424980, compound

HRID 408603Notes

Reaction equation

HRID 408603 reaction equation
[Cl:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][N:7]([CH2:26][C:27]#[N:28])[C:8]([C:10]2([CH3:25])[CH2:13][CH2:12][N:11]2[C:14](=[O:24])[CH2:15][C:16]2[CH:21]=[C:20]([CH3:22])[CH:19]=[C:18]([CH3:23])[CH:17]=2)=[O:9])=[CH:4][CH:3]=1.[Sn]([N:44]=[N+:45]=[N-:46])(CCCC)(CCCC)CCCC.Cl>C1(C)C=CC=CC=1.CCOCC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]([CH2:26][C:27]2[NH:46][N:45]=[N:44][N:28]=2)[C:8]([C:10]2([CH3:25])[CH2:13][CH2:12][N:11]2[C:14](=[O:24])[CH2:15][C:16]2[CH:21]=[C:20]([CH3:22])[CH:19]=[C:18]([CH3:23])[CH:17]=2)=[O:9])=[CH:29][CH:30]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4984872Tributyltin azideHCID 88859469HCID 88859469, compound

Product 1

HCID 178424980HCID 178424980, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 1-[2-(3,5-dimethyl-phenyl)-acetyl]-2-methyl-azetidine-2-carboxylic acid (4-chloro-benzyl)-cyanomethyl-amide, Compound 68 (1 eq.) in toluene was added Bu3SnN3 (10 eq.). The reaction was refluxed for 6 h and cooled to 20° C. then HCl 2N in Et2O was added. After 15 h of stirring, the solid was filtered, dissolved in DCM and precipitated with iPr2O. The solid was purified by chromatography on silica gel (elution with DCM/MeOH: 1/0 to 95/5) to afford 1-[2-(3,5-dimethyl-phenyl)-acetyl]-2-methyl-azetidine-2-carboxylic acid (4-chloro-benzyl)-(1H-tetrazol-5-ylmethyl)-amide.

Workup

  1. temperatureThe reaction was refluxed for 6 h
  2. filtrationthe solid was filtered
  3. dissolutiondissolved in DCM
  4. customprecipitated with iPr2O
  5. customThe solid was purified by chromatography on silica gel (elution with DCM/MeOH: 1/0 to 95/5)

Sources & evidence

ORD record
ord-479a928ee59d45338066600a2c54d37d
Source dataset
uspto-grants-2014_06
Patent number
US08759334B2

Reaction notes

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