1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (R)-N-(1-(3-chlorophenyl)ethyl)-4-methoxy-3-(morpholinosulfonyl)benzamide

HRID 1801581Notes

Reaction equation

HRID 1801581 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][C:4]=1[S:12]([N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)(=[O:14])=[O:13].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[Cl:42][C:43]1[CH:44]=[C:45]([C@H:49]([NH2:51])[CH3:50])[CH:46]=[CH:47][CH:48]=1>CN(C=O)C.CCOC(C)=O.O>[Cl:42][C:43]1[CH:44]=[C:45]([C@H:49]([NH:51][C:7](=[O:9])[C:6]2[CH:10]=[CH:11][C:3]([O:2][CH3:1])=[C:4]([S:12]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)(=[O:14])=[O:13])[CH:5]=2)[CH3:50])[CH:46]=[CH:47][CH:48]=1

Participants

8

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 7679134-Methoxy-3-(morpholine-4-sulfonyl)benzoic acidHCID 2507697(R)-1-(3-chlorophenyl)ethanamine

Product 1

HCID 26908119(R)-N-(1-(3-chlorophenyl)ethyl)-4-methoxy-3-(morpholinosulfonyl)benzamideYield 95.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-methoxy-3-(morpholinosulfonyl)benzoic acid 42 (0.824 g, 2.73 mmol) in DMF (6 mL) was added EDCI (0.686 g, 3.58 mmol) and HOBT (0.536 g, 3.50 mmol), the solution was stirred for 30 min and (R)-1-(3-chlorophenyl)ethanamine (0.673 g, 4.32 mmol) was added. The reaction mixture was stirred at room temperature for 16 h and diluted with EtOAc and water. The organic phase was washed with water (2×), brine (1×), dried over MgSO4, filtered, and concentrated in vacuo. Purification by flash column chromatography on silica gel (eluted with 60% to 100% EtOAc in hexanes) gave (R)—N-(1-(3-chlorophenyl)ethyl)-4-methoxy-3-(morpholinosulfonyl)benzamide 43 (1.14 g, 95.0% yield) as a white solid. Mass spectrum: calculated for C20H23ClN2O5S 438.1. found 439.1 (M++1).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 16 h
  2. washThe organic phase was washed with water (2×), brine (1×)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by flash column chromatography on silica gel (eluted with 60% to 100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-39ff14e12779404997a7c0d4e4b2f1c6
Source dataset
uspto-grants-2013_01
Patent number
US08349831B2

Reaction notes

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