1,2-Dichloroethane → N-{1-[Hydroxy-(5-pyridin-4-yl-[1,3,4]oxadiazol-2-yl)-methyl]-propyl}-4-oxo-2-benzylsulfonylmethyl-4-pyrrolidin-1-yl-butyramide

HRID 1830187Notes

Reaction equation

HRID 1830187 reaction equation
[O:1]=[C:2]([N:19]1[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]([OH:7])=O.OC(C(F)(F)F)=O.[NH2:31][CH:32]([CH2:46][CH3:47])[CH:33]([C:35]1[O:36][C:37]([C:40]2[CH:45]=[CH:44][N:43]=[CH:42][CH:41]=2)=[N:38][N:39]=1)[OH:34].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.CN1CCOCC1>C(Cl)Cl>[OH:34][CH:33]([C:35]1[O:36][C:37]([C:40]2[CH:41]=[CH:42][N:43]=[CH:44][CH:45]=2)=[N:38][N:39]=1)[CH:32]([NH:31][C:5](=[O:7])[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])[CH2:3][C:2](=[O:1])[N:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1)[CH2:46][CH3:47]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 220540034-Oxo-2-benzylsulfonylmethyl-4-pyrrolidin-1-yl-butyric acidHCID 866111392-amino-1-(5-pyridin-4-yl-[1,3,4]oxadiazol-2-yl)-butan-1-ol TFA salt

Product 1

HCID 22054105N-{1-[Hydroxy-(5-pyridin-4-yl-[1,3,4]oxadiazol-2-yl)-methyl]-propyl}-4-oxo-2-benzylsulfonylmethyl-4-pyrrolidin-1-yl-butyramideYield 126%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 4-oxo-2-benzylsulfonylmethyl-4-pyrrolidin-1-yl-butyric acid (102 mg, 0.3 mmol), 2-amino-1-(5-pyridin-4-yl-[1,3,4]oxadiazol-2-yl)-butan-1-ol TFA salt (105 mg), prepared as in reference 18, and HOBt (55 mg, 0.36 mmol) in MeCl2 (5 ml), was added EDC (86.4 mg, 0.45 mmol) and N-methylmorpholine (0.25 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 210 mg of N-{1-[Hydroxy-(5-pyridin-4-yl-[1,3,4]oxadiazol-2-yl)-methyl]-propyl}-4-oxo-2-benzylsulfonylmethyl-4-pyrrolidin-1-yl-butyramide. MS: 554.2(M−1), 555.8(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-9deab94c8ddc442baa8e0673d74adaef
Source dataset
uspto-grants-2006_06
Patent number
US07064123B1

Reaction notes

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