1,2-Dichloroethane → HCID 22054100, compound

HRID 1830181Notes

Reaction equation

HRID 1830181 reaction equation
[N:1]1([C:7](=[O:24])[CH2:8][CH:9]([CH2:13][S:14]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)(=[O:16])=[O:15])[C:10]([OH:12])=O)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.OC(C(F)(F)F)=O.[NH2:32][CH:33]([CH2:47][CH3:48])[CH:34]([C:36]1[O:37][C:38]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[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]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[N:39][N:40]=1)[CH:33]([NH:32][C:10](=[O:12])[CH:9]([CH2:13][S:14]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=[O:16])=[O:15])[CH2:8][C:7]([N:1]1[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1)=[O:24])[CH2:47][CH3:48]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 220539874-Morpholin-4-yl-4-oxo-2-benzylsulfonylmethyl-butyric acidHCID 86611138HCID 86611138, compound

Product 1

HCID 22054100HCID 22054100, compoundYield 107.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 4-morpholin-4-yl-4-oxo-2-benzylsulfonylmethyl-butyric acid (177 mg, 0.5 mmol), 2-amino-1-(5-phenyl-[1,3,4]oxadiazol-2-yl)-1-butanol TFA salt (175 mg), prepared as in reference 16, and HOBt (92 mg, 0.6 mmol) in MeCl2 (5 ml), was added EDC (144 mg, 0.75 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 308 mg of N-{1-[Hydroxy-(5-phenyl-[1,3,4]oxadiazol-2-yl)-methyl]-propyl}-4-morpholin-4-yl-4-oxo-2-benzylsulfonylmethyl-butyramide. Without further purification, the crude product was used for next reaction; MS: 569.6(M−1), 571.4(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-26eaeb7dfba545b4bc5a0d48e243a3a0
Source dataset
uspto-grants-2006_06
Patent number
US07064123B1

Reaction notes

Loading…