1-Chloroethyl chloroformate → HCID 86661738, compound

HRID 1961542Notes

Reaction equation

HRID 1961542 reaction equation
C([N:14]1[CH2:17][C:16]([C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH2:29][C:28]([C:34]4[CH:39]=[C:38]([Cl:40])[C:37]([Cl:41])=[C:36]([Cl:42])[CH:35]=4)([C:30]([F:33])([F:32])[F:31])[O:27][N:26]=3)=[CH:21][C:20]=2[Br:43])([F:18])[CH2:15]1)(C1C=CC=CC=1)C1C=CC=CC=1.ClC(OC(Cl)C)=O>CC#N.C(Cl)Cl>[Br:43][C:20]1[CH:21]=[C:22]([C:25]2[CH2:29][C:28]([C:34]3[CH:39]=[C:38]([Cl:40])[C:37]([Cl:41])=[C:36]([Cl:42])[CH:35]=3)([C:30]([F:33])([F:31])[F:32])[O:27][N:26]=2)[CH:23]=[CH:24][C:19]=1[C:16]1([F:18])[CH2:17][NH:14][CH2:15]1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 86661737HCID 86661737, compound

Product 1

HCID 86661738HCID 86661738, compoundYield 87.9%

Reagents, catalysts & solvents 1

HCID 21877088Acetonitrile methylene chlorideSolvent

Procedure

To a solution of 3-(4-(1-benzhydryl-3-fluoroazetidin-3-yl)-3-bromophenyl)-5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole (Preparation 29, 515 mg, 0.76 mmol) in MeCN/DCM (5:1, 60 mL) at 0° C. was added 1-chloroethyl chloroformate (275 uL, 2.5 mmol). The reaction was heated to reflux for 3 hours then allowed to cool to room temperature while stirring for 18 hours. Next, the reaction mixture was concentrated under vacuum, re-dissolved in anhydrous MeOH (50 mL), and refluxed for 1 hour. The reaction was cooled, concentrated under reduced pressure, and diethyl ether was added to residue. The resulting precipitate was filtered, rinsed with diethyl ether, and air dried to afford the intermediate (365 mg, 87%) as a solid. M/z (Cl) 713 ([M+H]+.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 3 hours
  3. concentrationNext, the reaction mixture was concentrated under vacuum
  4. dissolutionre-dissolved in anhydrous MeOH (50 mL)
  5. temperaturerefluxed for 1 hour
  6. temperatureThe reaction was cooled
  7. concentrationconcentrated under reduced pressure, and diethyl ether
  8. additionwas added to residue
  9. filtrationThe resulting precipitate was filtered
  10. washrinsed with diethyl ether, and air
  11. customdried

Sources & evidence

ORD record
ord-3e689b2da2464d10aa0a99cfe0a56b2b
Source dataset
uspto-grants-2013_04
Patent number
US08415310B2

Reaction notes

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