4-Methylmorpholine → ethyl (2S)-2-[3-(4-methoxyphenyl)propanoylamino]-3-[4-[[5-(N-phenylmethoxycarbonylcarbamimidoyl)-1-benzofuran-2-carbonyl]amino]phenyl]propanoate

HRID 1291015Notes

Reaction equation

HRID 1291015 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]([C:14]1[CH:15]=[CH:16][C:17]2[O:21][C:20]([C:22](O)=[O:23])=[CH:19][C:18]=2[CH:25]=1)=[NH:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33][C@H:34]([NH:40][C:41](=[O:52])[CH2:42][CH2:43][C:44]2[CH:49]=[CH:48][C:47]([O:50][CH3:51])=[CH:46][CH:45]=2)[C:35]([O:37][CH2:38][CH3:39])=[O:36])=[CH:29][CH:28]=1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CN1CCOCC1>CN(C)C=O.O>[CH2:1]([O:8][C:9]([NH:11][C:12]([C:14]1[CH:15]=[CH:16][C:17]2[O:21][C:20]([C:22]([NH:26][C:27]3[CH:32]=[CH:31][C:30]([CH2:33][C@H:34]([NH:40][C:41](=[O:52])[CH2:42][CH2:43][C:44]4[CH:45]=[CH:46][C:47]([O:50][CH3:51])=[CH:48][CH:49]=4)[C:35]([O:37][CH2:38][CH3:39])=[O:36])=[CH:29][CH:28]=3)=[O:23])=[CH:19][C:18]=2[CH:25]=1)=[NH:13])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 2724699PyBOPHCID 54293664ethyl (S)-3-(4-aminophenyl)-2-[3-(4-methoxyphenyl)propionylamino]propionateHCID 1403812485-(N-phenylmethoxycarbonylcarbamimidoyl)-1-benzofuran-2-carboxylic acid

Product 1

HCID 141572816ethyl (2S)-2-[3-(4-methoxyphenyl)propanoylamino]-3-[4-[[5-(N-phenylmethoxycarbonylcarbamimidoyl)-1-benzofuran-2-carbonyl]amino]phenyl]propanoateYield 88.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

5-(Benzyloxycarbonylamidino)-2-benzofurancarboxylic acid (151 mg, 0.447 mmol) and ethyl (S)-3-(4-aminophenyl)-2-[3-(4-methoxyphenyl)propionylamino]propionate (165 mg, 0.445 mmol) were dissolved in N,N-dimethylformamide (10 ml), and PyBOP (benzotriazol-1-yl-oxy-tris(pyrrolidino)phosphonium hexafluorophosphate) (225 mg, 0.490 mmol) and N-methylmorpholine (0.05 ml, 0.455 mmol) were added. The mixture was stirred at room temperature for 15 hours. Water (20 ml) was added to the reaction mixture, and the resulting precipitate was collected by filtration and washed with water to give 271 mg of ethyl (S)-3-[4-[[5-(benzyloxycarbonylamidino)-2-benzofuranyl]carbonylamino]phenyl]-2-[3-(4-methoxyphenyl)propionylamino]propionate as a colorless solid (88%).

Workup

  1. filtrationthe resulting precipitate was collected by filtration
  2. washwashed with water

Sources & evidence

ORD record
ord-b444ebc37dff4e26b9d9af417a56af02
Source dataset
uspto-grants-1998_05
Patent number
US05753670

Reaction notes

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