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

HRID 1682676Notes

Reaction equation

HRID 1682676 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 (151mg, 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 271mg 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-106b9db67ab144e7a243451009eb36b6
Source dataset
uspto-grants-1997_06
Patent number
US05635527

Reaction notes

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