1,2-Dichloroethane → N-(2-benzooxazol-2-yl-2-hydroxy-1-methoxymethyl-ethyl)-2-(2-difluoromethoxy-benzylsulfonylmethyl)-4-morpholin-4-yl-4-oxo-butyramide

HRID 1830196Notes

Reaction equation

HRID 1830196 reaction equation
[F:1][CH:2]([F:28])[O:3][C:4]1[CH:27]=[CH:26][CH:25]=[CH:24][C:5]=1[CH2:6][S:7]([CH2:10][CH:11]([CH2:15][C:16]([N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1)=[O:17])[C:12](O)=[O:13])(=[O:9])=[O:8].[NH2:29][CH:30]([CH2:42][O:43][CH3:44])[CH:31]([C:33]1[O:34][C:35]2[CH:41]=[CH:40][CH:39]=[CH:38][C:36]=2[N:37]=1)[OH:32].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.CN1CCOCC1>C(Cl)Cl>[O:34]1[C:35]2[CH:41]=[CH:40][CH:39]=[CH:38][C:36]=2[N:37]=[C:33]1[CH:31]([OH:32])[CH:30]([NH:29][C:12](=[O:13])[CH:11]([CH2:10][S:7]([CH2:6][C:5]1[CH:24]=[CH:25][CH:26]=[CH:27][C:4]=1[O:3][CH:2]([F:28])[F:1])(=[O:8])=[O:9])[CH2:15][C:16]([N:18]1[CH2:19][CH2:20][O:21][CH2:22][CH2:23]1)=[O:17])[CH2:42][O:43][CH3:44]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 220540252-(2-Difluoromethoxy-benzylsulfonylmethyl)-4-morpholin-4-yl-4-oxo-butyric acidHCID 220541122-Amino-1-benzooxazol-2-yl-3-methoxy-propan-1-ol

Product 1

HCID 22053962N-(2-benzooxazol-2-yl-2-hydroxy-1-methoxymethyl-ethyl)-2-(2-difluoromethoxy-benzylsulfonylmethyl)-4-morpholin-4-yl-4-oxo-butyramideYield 96.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 2-(2-difluoromethoxy-benzylsulfonylmethyl)-4-morpholin-4-yl-4-oxo-butyric acid (210.5 mg, 0.5 mmol), 2-amino-1-benzooxazol-2-yl-3-methoxy-propan-1-ol (112.5 mg), and HOBt (91.8 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 301 mg of N-(2-benzooxazol-2-yl-2-hydroxy-1-methoxymethyl-ethyl)-2-(2-difluoromethoxy-benzylsulfonylmethyl)-4-morpholin-4-yl-4-oxo-butyramide; MS: 624.5(M−1), 626.3(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-d444d0dc214e4efabf441746ed9039e9
Source dataset
uspto-grants-2006_06
Patent number
US07064123B1

Reaction notes

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