1,2-Dichloroethane → Morpholine-4-carboxylic acid (1-{1-[hydroxy-(5-phenyl-[1,3,4]oxadiazol-2-yl)-methyl]-pentylcarbamoyl}-2-phenylmethane-sulfonyl-ethyl)-amide

HRID 489635Notes

Reaction equation

HRID 489635 reaction equation
[N:1]1([C:7]([NH:9][CH:10]([CH2:14][S:15]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)(=[O:17])=[O:16])[C:11](O)=[O:12])=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.OC(C(F)(F)F)=O.[NH2:32][CH:33]([CH2:47][CH2:48][CH2:49][CH3:50])[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:11]([CH:10]([NH:9][C:7]([N:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1)=[O:8])[CH2:14][S:15]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(=[O:17])=[O:16])=[O:12])[CH2:47][CH2:48][CH2:49][CH3:50]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 112797342-[(Morpholine-4-carbonyl)-amino]-3-phenylmethanesulfonyl-propionic acidHCID 865900212-amino-1-(5-phenyl-[1,3,4]oxadiazol-2-yl)-1-hexanol TFA salt

Product 1

HCID 86590020Morpholine-4-carboxylic acid (1-{1-[hydroxy-(5-phenyl-[1,3,4]oxadiazol-2-yl)-methyl]-pentylcarbamoyl}-2-phenylmethane-sulfonyl-ethyl)-amideYield 69.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 2-[(morpholine-4-carbonyl)-amino]-3-phenylmethane-sulfonyl-propionic acid (135 mg, 0.37 mmol), 2-amino-1-(5-phenyl-[1,3,4]oxadiazol-2-yl)-1-hexanol TFA salt (135 mg, 0.36 mmol), prepared as in Reference 1, and HOBt (66 mg, 0.43 mmol) in MeCl2 (5 ml), was added EDC (103.6 mg, 0.54 mmol) and N-methylmorpholine (0.4 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. The residue was subjected to silica gel column chromatography to yield morpholine-4-carboxylic acid (1-{1-[hydroxy-(5-phenyl-[1,3,4]oxadiazol-2-yl)-methyl]-pentylcarbamoyl}-2-phenylmethane-sulfonyl-ethyl)-amide (150 mg); MS: 598.6 (M−1), 600.6 (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-c7ad210da3ec406da9c3b9eed339941e
Source dataset
uspto-grants-2005_12
Patent number
US06977256B2

Reaction notes

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