5-(N-phenylmethoxycarbonylcarbamimidoyl)-1-benzofuran-2-carboxylic acid → HCID 178449149, compound

HRID 1291026Notes

Reaction equation

HRID 1291026 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]([CH2:38][C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:34][CH2:35][CH2:36][CH3:37])[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]([CH2:38][C:39]([O:41][C:42]([CH3:43])([CH3:45])[CH3:44])=[O:40])[CH2:34][CH2:35][CH2:36][CH3:37])[CH2:31][CH2:32]3)=[O:24])=[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

3

Reactant 2

HCID 1403812485-(N-phenylmethoxycarbonylcarbamimidoyl)-1-benzofuran-2-carboxylic acidHCID 178449148HCID 178449148, compound

Product 1

HCID 178449149HCID 178449149, compoundYield 75.6%

Procedure

In the same manner as in Example 15 (3), 5-(benzyloxycarbonylamidino)-2-benzofurancarboxylic acid (785 mg, 2.32 mmol) and t-butyl trans-(4-aminocyclohexyl-N-n-butylamino)acetate (680 mg, 2.32 mmol) were condensed and purified by silica gel column chromatography (n-hexane/ethyl acetate=1/1-1/4) to give 1.06 g of t-butyl trans-[4-[[5-(benzyloxycarbonylamidino)-2-benzofuranyl)carbonylamino)cyclohexyl-N-n-butylamino]acetate as a colorless solid (75%).

Workup

  1. customcondensed
  2. custompurified by silica gel column chromatography (n-hexane/ethyl acetate=1/1-1/4)

Sources & evidence

ORD record
ord-2c963952bab046408ade4dc0a9a3dcc7
Source dataset
uspto-grants-1998_05
Patent number
US05753670

Reaction notes

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