5-(N-phenylmethoxycarbonylcarbamimidoyl)-1-benzofuran-2-carboxylic acid → HCID 178451304, compound

HRID 1682672Notes

Reaction equation

HRID 1682672 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]([OH:24])=O)=[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@H:27]1[CH2:32][CH2:31][C@H:30]([N:33]([CH2:41][C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:29][CH2:28]1>>[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@H:27]3[CH2:28][CH2:29][C@H:30]([N:33]([CH2:41][C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[C:34]([O:36][C:37]([CH3:38])([CH3:39])[CH3:40])=[O:35])[CH2:31][CH2:32]3)=[O:24])=[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

Participants

3

Reactant 2

HCID 1403812485-(N-phenylmethoxycarbonylcarbamimidoyl)-1-benzofuran-2-carboxylic acidHCID 178451303HCID 178451303, compound

Product 1

HCID 178451304HCID 178451304, compoundYield 37.3%

Procedure

In the same manner as in Example 15 (3), 5-(benzyloxycarbonylamidino)-2-benzofurancarboxylic acid (690 mg, 2.04 mmol) and t-butyl trans -[4-aminocyclohexyl-N-(t-butoxycarbonyl)amino]acetate (670 mg, 2.04 mmol) were condensed and purified by silica gel column chromatography (n-hexane/ethyl acetate=2/3) to give 493 mg of t-butyl trans-[4-[[5-(benzyloxycarbonylamidino)-2-benzofuranyl]carbonylamino]cyclohexyl-N-(t-butoxycarbonyl)amino]acetate as a colorless solid (37%).

Workup

  1. customcondensed
  2. custompurified by silica gel column chromatography (n-hexane/ethyl acetate=2/3)

Sources & evidence

ORD record
ord-c1028706c16849bea42f79e556db6bb5
Source dataset
uspto-grants-1997_06
Patent number
US05635527

Reaction notes

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