Ethylenediaminetetraacetic Acid → HCID 136377641, compound
Reaction equation
[P:1]([O:9][CH2:10][C@H:11]1[O:15][C@@H:14]([N:16]2[C:26]3[N:25]=[C:23]([NH2:24])[NH:22][C:20](=[O:21])[C:19]=3[N:18](C)[CH2:17]2)[C@H:13]([OH:28])[CH2:12]1)([O:4][P:5]([OH:8])([OH:7])=[O:6])(=[O:3])[OH:2].C(N(CC(O)=O)CC(O)=O)CN(CC(O)=O)CC(O)=O.C([O-])(O)=O.[Na+]>CN(C=O)C.O.[Cl-].[Cl-].[Zn+2]>[P:1]([O:9][CH2:10][C@H:11]1[O:15][C@@H:14]([N:16]2[C:26]3[N:25]=[C:23]([NH2:24])[NH:22][C:20](=[O:21])[C:19]=3[N:18]=[CH:17]2)[C@H:13]([OH:28])[CH2:12]1)([O:4][P:5]([OH:7])([OH:8])=[O:6])(=[O:2])[OH:3]Participants
Procedure
GMP (purchased from Sigma, converted to the TEA salt, 29 mg, 0.05 mmol), imidazole (17 mg, 0.25 mmol), and 2,2′-dithiodipyridine (22 mg, 0.1 mmol, purchased from Aldrich) were mixed in anhydrous DMF (1.2 mL) and TEA (7 μL). Triphenylphosphine (26 mg, 0.1 mmol) was added, and the mixture was stirred for 5 h at room temperature. The mixture was placed in a centrifuge tube, and sodium perchlorate (25 mg, anhydrous) dissolved in acetone (6 mL) was added. The procedure for washing the precipitate with acetone and drying over P4O10 was the same as for Compound 5. The imidazolide of GMP thus obtained was dissolved in DMF (1.2 mL), and Compound 7 (10 mg, TEA salt, 0.015 mmol) was added. Next ZnCl2 (40 mg) was added. The mixture was stirred at room temperature overnight, poured into a beaker containing a solution of 125 mg of EDTA in 15 mL of water, and neutralized with 1 M NaHCO3. Chromatographic isolation as for Compound 5 gave Compound 9 (13 mg, 88% based on the amount of Compound 7 used).
Workup
- additionpoured into a beaker
Sources & evidence
- ORD record
- ord-0bd35f1dbed94cb695d4a4bbb4cd503e
- Source dataset
- uspto-grants-2006_07
- Patent number
- US07074596B2
Reaction notes
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