Ethyl 2-formyl-3-oxopropanoate → 1-[6-{[bis-(4-methoxy-phenyl)-methyl]-amino}-9-((1R,2S,3R,4S)-2,3-dihydroxy-4-propionylamino-cyclopentyl)-9H-purin-2-yl]-1H-pyrazole-4-carboxylic acid ethyl ester

HRID 2382451Notes

Reaction equation

HRID 2382451 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([NH:18][C:19]2[N:27]=[C:26]([NH:28][NH2:29])[N:25]=[C:24]3[C:20]=2[N:21]=[CH:22][N:23]3[C@@H:30]2[CH2:34][C@H:33]([NH:35][C:36](=[O:39])[CH2:37][CH3:38])[C@@H:32]([OH:40])[C@H:31]2[OH:41])[C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[CH:5][CH:4]=1.[CH2:42]([O:44][C:45](=[O:51])[CH:46]([CH:49]=O)[CH:47]=O)[CH3:43]>C(O)C>[CH2:42]([O:44][C:45]([C:46]1[CH:47]=[N:29][N:28]([C:26]2[N:25]=[C:24]3[C:20]([N:21]=[CH:22][N:23]3[C@@H:30]3[CH2:34][C@H:33]([NH:35][C:36](=[O:39])[CH2:37][CH3:38])[C@@H:32]([OH:40])[C@H:31]3[OH:41])=[C:19]([NH:18][CH:9]([C:10]3[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=3)[C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=3)[N:27]=2)[CH:49]=1)=[O:51])[CH3:43]

Participants

4

Reactant 2

HCID 11029955Ethyl 2-formyl-3-oxopropanoateHCID 66631032N-[(1S,2R,3S,4R)-4-(6-{[Bis-(4-methoxy-phenyl)-methyl]-amino}-2-hydrazino-purin-9-yl)-2,3-dihydroxy-cyclopentyl]-propionamide

Product 1

HCID 666310101-[6-{[bis-(4-methoxy-phenyl)-methyl]-amino}-9-((1R,2S,3R,4S)-2,3-dihydroxy-4-propionylamino-cyclopentyl)-9H-purin-2-yl]-1H-pyrazole-4-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of N-[(1S,2R,3S,4R)-4-(6-{[Bis-(4-methoxy-phenyl)-methyl]-amino}-2-hydrazino-purin-9-yl)-2,3-dihydroxy-cyclopentyl]-propionamide (0.1 g, 0.177 mmol) in dry ethyl alcohol (5 ml) is added 2-formyl-3-oxo-propionic acid ethyl ester (synthesised from ethyl-3,3-diethoxy-propionate, as described in: Bertz S. H., Dabbagh G. and Cotte P.; J. Org. Chem. (1982) 47, pp 2216-2217) (0.033 g, 0.231 mmol). The reaction mixture is heated at reflux for 8 hours then concentrated in vacuo. The crude residue is purified by chromatography on silica (60-120 mesh) eluting with 3% methanol in chloroform to afford the title compound. LC-MS (0.1% formic acid, acetonitrile): (MH+ 671).

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 8 hours
  3. concentrationthen concentrated in vacuo
  4. customThe crude residue is purified by chromatography on silica (60-120 mesh)
  5. washeluting with 3% methanol in chloroform

Sources & evidence

ORD record
ord-d2ad10094fba43bf8a5ce61c8bcaa5fc
Source dataset
uspto-grants-2012_09
Patent number
US08258141B2

Reaction notes

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