1,2-Dichloroethane → N-{1-[hydroxy-(5-methoxymethyl-[1,3,4]oxadiazol-2-yl)-methyl]-propyl}-4-oxo-2-benzylsulfonylmethyl-4-piperidin-1-yl-butyramide

HRID 1830177Notes

Reaction equation

HRID 1830177 reaction equation
[O:1]=[C:2]([N:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)[CH2:3][CH:4]([CH2:8][S:9]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[O:11])=[O:10])[C:5](O)=[O:6].O[C:26](C(F)(F)F)=O.[NH2:32][CH:33]([CH3:44])[CH:34]([C:36]1[O:37][C:38]([CH2:41][O:42][CH3:43])=[N:39][N:40]=1)[OH:35].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.CN1CCOCC1>C(Cl)Cl>[OH:35][CH:34]([C:36]1[O:37][C:38]([CH2:41][O:42][CH3:43])=[N:39][N:40]=1)[CH:33]([NH:32][C:5](=[O:6])[CH:4]([CH2:8][S:9]([CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)(=[O:11])=[O:10])[CH2:3][C:2](=[O:1])[N:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)[CH2:44][CH3:26]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 220539604-Oxo-2-benzylsulfonylmethyl-4-piperidin-1-yl-butyric acidHCID 866111372-amino-1-(5-methoxymethyl-1,3,4-oxadiazole-2-yl)-1-propanol TFA salt

Product 1

HCID 22054075N-{1-[hydroxy-(5-methoxymethyl-[1,3,4]oxadiazol-2-yl)-methyl]-propyl}-4-oxo-2-benzylsulfonylmethyl-4-piperidin-1-yl-butyramideYield 37.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 4-oxo-2-benzylsulfonylmethyl-4-piperidin-1-yl-butyric acid (229 mg, 0.65 mmol), 2-amino-1-(5-methoxymethyl-1,3,4-oxadiazole-2-yl)-1-propanol TFA salt (204 mg), prepared as in reference 15, and HOBt (119 mg, 0.78 mmol) in MeCl2 (5 ml), was added EDC (187 mg, 0.98 mmol) and N-methylmorpholine (0.35 ml) at room temperature. After stirring for 14 hours, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated NaHCO3, brine, dried with MgSO4 and concentrated to yield 130 mg of N-{1-[hydroxy-(5-methoxymethyl-[1,3,4]oxadiazol-2-yl)-methyl]-propyl}-4-oxo-2-benzylsulfonylmethyl-4-piperidin-1-yl-butyramide; MS: 535.4(M−1), 537.7(M+1).

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated NaHCO3, brine
  3. dry with materialdried with MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-56212c6bdc8146c09a34a12549e0a6a4
Source dataset
uspto-grants-2006_06
Patent number
US07064123B1

Reaction notes

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