1-Chloroethyl chloroformate → HCID 9867172, compound

HRID 397632Notes

Reaction equation

HRID 397632 reaction equation
ClC(OC(Cl)C)=O.C([N:15]1[CH2:20][CH2:19][CH:18]([O:21][CH2:22][C:23]2[O:27][N:26]=[C:25]([C@@H:28]3[CH2:33][CH2:32][CH2:31][CH2:30][N:29]3[S:34]([CH2:37][CH:38]3[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]3)(=[O:36])=[O:35])[N:24]=2)[CH2:17][CH2:16]1)C1C=CC=CC=1>ClCCl>[CH:38]1([CH2:37][S:34]([N:29]2[CH2:30][CH2:31][CH2:32][CH2:33][C@H:28]2[C:25]2[N:24]=[C:23]([CH2:22][O:21][CH:18]3[CH2:17][CH2:16][NH:15][CH2:20][CH2:19]3)[O:27][N:26]=2)(=[O:36])=[O:35])[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 9914530HCID 9914530, compound

Product 1

HCID 9867172HCID 9867172, compoundYield 63.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

α-Chloroethyl chloroformate (95 μl) was added to a solution of 5-[(1-benzyl-4-piperidyl)oxymethyl]-3-[(2S)-1-cyclohexylmethylsulfonyl-2-piperidyl]-1,2,4-oxadiazole (325 mg) [see Example 16] in dichloromethane (20 ml) at 0° C. The reaction mixture was stirred for 1.5 hours after which time the dichloromethane was removed under reduced pressure and the residue dissolved in methanol. The mixture was then heated under reflux for 2 hours, the solvent removed under reduced pressure and the residue partitioned between diethyl ether and 2N aqueous hydrochloric acid solution. The aqueous layer was washed twice with diethyl ether and then neutralised (pH7) with sodium hydrogen carbonate. The aqueous layer was extracted with ethyl acetate, dried over magnesium sulphate and the solvent removed under reduced pressure to afford 3-[(2S)-1-cyclohexylmethylsulfonyl-2-piperidyl]-5-[4-piperidyloxymethyl]-1,2,4-oxadiazole (170 mg) as a brown oil.

Workup

  1. customwas removed under reduced pressure
  2. dissolutionthe residue dissolved in methanol
  3. temperatureThe mixture was then heated
  4. temperatureunder reflux for 2 hours
  5. customthe solvent removed under reduced pressure
  6. customthe residue partitioned between diethyl ether and 2N aqueous hydrochloric acid solution
  7. washThe aqueous layer was washed twice with diethyl ether
  8. extractionThe aqueous layer was extracted with ethyl acetate
  9. dry with materialdried over magnesium sulphate
  10. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-4d30007d2a3a4f94b81954dfbe407ad7
Source dataset
uspto-grants-2003_08
Patent number
US06610707B1

Reaction notes

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