Potassium Iodide → HCID 145821438, compound

HRID 1757013Notes

Reaction equation

HRID 1757013 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]([C:14]1[CH:19]=[CH:18][C:17]([N:20]2[CH2:25][CH2:24][CH:23]([C:26](N3CCC(CC(O)=O)CC3)=[O:27])[CH2:22][CH2:21]2)=[CH:16][CH:15]=1)=[NH:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:38]([O:44][CH2:45]Cl)(=[O:43])[C:39]([CH3:42])([CH3:41])[CH3:40].[I-].[K+].[C:49](=[O:52])(O)[O-:50].[K+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C.O>[CH2:1]([O:8][C:9]([NH:11][C:12]([C:14]1[CH:19]=[CH:18][C:17]([N:20]2[CH2:25][CH2:24][CH:23]([C:26]([CH:21]3[CH2:22][CH:23]([CH2:26][C:49]([O:50][CH2:45][O:44][C:38](=[O:43])[C:39]([CH3:42])([CH3:41])[CH3:40])=[O:52])[CH2:24][CH2:25][NH:20]3)=[O:27])[CH2:22][CH2:21]2)=[CH:16][CH:15]=1)=[NH:13])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

9

Reactant 5

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 87885Chloromethyl pivalateHCID 516893Potassium BicarbonateHCID 145821449HCID 145821449, compound

Product 1

HCID 145821438HCID 145821438, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A suspension of 1 equivalent of 1-[4-(N-benzyloxycarbonylamidino)-phenyl]-4-[4-(carboxymethyl)-piperidinocarbonyl]-piperidine is stirred for 2 days with 2 equivalents each of chloromethyl pivalate, potassium iodide, potassium bicarbonate and potassium carbonate in dimethylformamide at ambient temperature for 2 days. After pouring into water, extraction with ethyl acetate and evaporation down of the ethyl acetate extract, the desired product is obtained which is then chromotagraphed over silica gel. The following compounds are obtained analogously to Example 10:

Workup

  1. extractionextract

Sources & evidence

ORD record
ord-29c0065ecb0e448990ca16c855f2d5ae
Source dataset
uspto-grants-1995_08
Patent number
US05442064

Reaction notes

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