1,2-Dichloroethane → HCID 22054011, compound

HRID 1830192Notes

Reaction equation

HRID 1830192 reaction equation
[CH:1]1([CH2:7][CH:8]([CH2:12][C:13]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)=[O:14])[C:9]([OH:11])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.OC(C(F)(F)F)=O.[NH2:28][CH:29]([CH2:43][CH3:44])[CH:30]([C:32]1[O:33][C:34]([C:37]2[CH:42]=[CH:41]C=CC=2)=N[N:36]=1)[OH:31].C1C=CC2N(O)N=[N:51][C:49]=2C=1.C(Cl)CCl.CN1CCOCC1>C(Cl)Cl>[CH:1]1([CH2:7][CH:8]([CH2:12][C:13]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)=[O:14])[C:9]([NH:28][CH:29]([CH:30]([OH:31])[C:32]2[O:33][C:34]3[C:49]([N:36]=2)=[N:51][CH:41]=[CH:42][CH:37]=3)[CH2:43][CH3:44])=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 218998342-Cyclohexylmethyl-4-morpholin-4-yl-4-oxobutyric acidHCID 86611138HCID 86611138, compound

Product 1

HCID 22054011HCID 22054011, compoundYield 115.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stiffed mixture of 2-cyclohexylmethyl-4-morpholin-4-yl-4-oxo-butyric acid (84.9 mg, 0.3 mmol), 2-amino-1-(5-phenyl-[1,3,4]oxadiazol-2-yl)-1-butanol TFA salt (97.5 mg), prepared as in reference 21, and HOBt (55.1 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 153 mg of 2-cyclohexylmethyl-N-[1-(hydroxy-oxazolo[4,5-b]pyridin-2-yl-methyl)-propyl]-4-morpholin-4-yl-4-oxo-butyramide; MS: 471.6(M−1), 473.3(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-2016c5dca5a54b7085f3e7b125e0e912
Source dataset
uspto-grants-2006_06
Patent number
US07064123B1

Reaction notes

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