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

HRID 1830179Notes

Reaction equation

HRID 1830179 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.O[C:25](C(F)(F)F)=O.[NH2:31][CH:32]([CH3:43])[CH:33]([C:35]1[O:36][C:37]([CH2:40][O:41][CH3:42])=[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]([CH2:40][O:41][CH3:42])=[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)[CH2:43][CH3:25]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 220540034-Oxo-2-benzylsulfonylmethyl-4-pyrrolidin-1-yl-butyric acidHCID 866111372-amino-1-(5-methoxymethyl-1,3,4-oxadiazole-2-yl)-1-propanol TFA salt

Product 1

HCID 22054041N-{1-[Hydroxy-(5-methoxymethyl-[1,3,4]oxadiazol-2-yl)-methyl]-propyl}-4-oxo-2-benzylsulfonylmethyl-4-pyrrolidin-1-yl-butyramideYield 24.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 4-oxo-2-benzylsulfonylmethyl-4-pyrrolidin-1-yl-butyric acid (220 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 84 mg of N-{1-[Hydroxy-(5-methoxymethyl-[1,3,4]oxadiazol-2-yl)-methyl]-propyl}-4-oxo-2-benzylsulfonylmethyl-4-pyrrolidin-1-yl-butyramide. Without further purification, the crude product was used for next reaction; MS: 521.6(M−1), 523.2(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-96a4fad319674de6b3065619434beff5
Source dataset
uspto-grants-2006_06
Patent number
US07064123B1

Reaction notes

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