Ethylmorpholine → N-{2-(4-Chlorophenyl)-1-[(2,2-diethoxyethyl)isopropylcarbamoyl]ethyl}-3-(2,4-dichlorobenzenesulfonylamino)-2-methanesulfonylaminopropionamide

HRID 1670499Notes

Reaction equation

HRID 1670499 reaction equation
C1C=CC2N(O)N=NC=2C=1.C(N1CCOCC1)C.C(OC([NH:29][CH:30]([CH2:34][NH:35][S:36]([C:39]1[CH:44]=[CH:43][C:42]([Cl:45])=[CH:41][C:40]=1[Cl:46])(=[O:38])=[O:37])[C:31]([OH:33])=O)=O)C1C=CC=CC=1.[NH2:47][CH:48]([CH2:63][C:64]1[CH:69]=[CH:68][C:67]([Cl:70])=[CH:66][CH:65]=1)[C:49]([N:51]([CH2:55][CH:56]([O:60][CH2:61][CH3:62])[O:57][CH2:58][CH3:59])[CH:52]([CH3:54])[CH3:53])=[O:50]>CN(C=O)C.C(Cl)CCl>[Cl:70][C:67]1[CH:66]=[CH:65][C:64]([CH2:63][CH:48]([NH:47][C:31](=[O:33])[CH:30]([NH:29][S:36]([CH3:39])(=[O:38])=[O:37])[CH2:34][NH:35][S:36]([C:39]2[CH:44]=[CH:43][C:42]([Cl:45])=[CH:41][C:40]=2[Cl:46])(=[O:37])=[O:38])[C:49](=[O:50])[N:51]([CH2:55][CH:56]([O:60][CH2:61][CH3:62])[O:57][CH2:58][CH3:59])[CH:52]([CH3:54])[CH3:53])=[CH:69][CH:68]=1

Participants

7

Reactant 4

HCID 7525EthylmorpholineHCID 757711-HydroxybenzotriazoleHCID 673394042-Benzyloxycarbonylamino-3-(2,4-dichlorobenzenesulfonylamino)propionic acidHCID 673416462-amino-3-(4-chlorophenyl)-N-(2,2-diethoxyethyl)-N-isopropylpropionamide

Product 1

HCID 67340421N-{2-(4-Chlorophenyl)-1-[(2,2-diethoxyethyl)isopropylcarbamoyl]ethyl}-3-(2,4-dichlorobenzenesulfonylamino)-2-methanesulfonylaminopropionamide

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolvent2×

Procedure

52 mg of EDC, 45 mg of HOBt and 100 μl of N-ethylmorpholine are added to a solution of 124 mg of 2-benzyloxycarbonylamino-3-(2,4-dichlorobenzenesulfonylamino)propionic acid in 1 ml of DMF. A solution of 100 mg of 2-amino-3-(4-chlorophenyl)-N-(2,2-diethoxyethyl)-N-isopropylpropionamide in 1 ml of DMF is added dropwise thereto, and the solution is left to stir for 12 h. The reaction solution is filtered, mixed with ethyl acetate and then extracted with 5% aqueous sodium bicarbonate solution and aqueous sodium chloride solution. Drying of the organic phase over sodium sulfate is followed by concentration under reduced pressure, and the residue is separated by HPLC (Knauer Eurospher-100-10-C18, water (0.1% trifluoroacetic acid)/acetonitrile (0.1% trifluoroacetic acid)=80/20→10/90). The desired product is obtained with MW=784.186 (calculated); measured value (M−CO2+H)+: 741.10.

Workup

  1. waitthe solution is left
  2. filtrationThe reaction solution is filtered
  3. additionmixed with ethyl acetate
  4. extractionextracted with 5% aqueous sodium bicarbonate solution and aqueous sodium chloride solution
  5. dry with materialDrying of the organic phase over sodium sulfate
  6. concentrationis followed by concentration under reduced pressure
  7. customthe residue is separated by HPLC (Knauer Eurospher-100-10-C18, water (0.1% trifluoroacetic acid)/acetonitrile (0.1% trifluoroacetic acid)=80/20→10/90)

Sources & evidence

ORD record
ord-682df87d12e9445f95ee9c28342716ee
Source dataset
uspto-grants-2011_08
Patent number
US07994168B2

Reaction notes

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