Diethyl Ether → HCID 178469237, compound

HRID 2351828Notes

Reaction equation

HRID 2351828 reaction equation
C(=O)(O)O.[CH2:5]([O:7][C:8]([CH:10]1[CH2:15][CH2:14][N:13]([C:16]([NH2:18])=[O:17])[CH2:12][CH2:11]1)=[O:9])[CH3:6].[NH:19]([C:23]1[CH:49]=[CH:48][C:26]([C:27]([NH:29][CH:30]([C:45]([OH:47])=[O:46])[CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([O:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[CH:33]=2)=[O:28])=[CH:25][CH:24]=1)[C:20]([NH2:22])=[NH:21].[CH3:50][S:51]([OH:54])(=[O:53])=[O:52].C(OCC)C>CO>[CH3:50][S:51]([OH:54])(=[O:53])=[O:52].[CH2:5]([O:7][C:8]([CH:10]1[CH2:15][CH2:14][N:13]([C:16]([NH2:18])=[O:17])[CH2:12][CH2:11]1)=[O:9])[CH3:6].[NH:19]([C:23]1[CH:24]=[CH:25][C:26]([C:27]([NH:29][CH:30]([C:45]([OH:47])=[O:46])[CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([O:38][C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)[CH:33]=2)=[O:28])=[CH:48][CH:49]=1)[C:20]([NH2:22])=[NH:21]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6395Methanesulfonic AcidHCID 178469238HCID 178469238, compound

Product 1

HCID 178469237HCID 178469237, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (II) (0.7 g) and 4-guanidinobenzoic acid (0.36 g) were dissolved in dry pyridine (20 ml) and the above-mentioned condensation agent was then added, followed by allowing to stand at room temperature for 24 hours. After the reaction, the solvent was distilled off and the residue was washed several times with a saturated aqueous sodium bicarbonate solution. Thus, N-(4-guanidinobenzoyl)-3-phenoxy-DL-phenylalanine 4-ethoxycarbonylpiperidinoamide carbonate (III) (0.65 g) was obtained in the form of yellowish brown solid. The compound (III) (0.65 g) was dissolved in methanol (5 ml) and methanesulfonic acid (0.11 g) was added to the resultant solution. The mixture was allowed to stand for 30 minutes and diethyl ether was added thereto. The precipitated solid was washed several times with diethyl ether to obtain N-(4-guanidinobenzoyl)-3-phenoxy-DL-phenylalanine 4-ethoxycarbonylpiperidinoamide methane sulfonate (IV) (0.67 g) (i.e., Compound No. 34) in the form of a pale brown solid.

Workup

  1. washThe precipitated solid was washed several times with diethyl ether

Sources & evidence

ORD record
ord-5c70529ad0fc48b6bdca53dbfb242ab2
Source dataset
uspto-grants-1989_10
Patent number
US04873253

Reaction notes

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