Adipic Acid → HCID 136333635, compound

HRID 1005360Notes

Reaction equation

HRID 1005360 reaction equation
[C@@H:1]1([N:10]2[C:20]3[N:19]=[C:17]([NH2:18])[NH:16][C:14](=[O:15])[C:13]=3[N:12]=[CH:11]2)[O:9][C@H:6]([CH2:7][OH:8])[C@@H:4]([OH:5])[C@H:2]1[OH:3].[C:21](O)(=[O:29])[CH2:22][CH2:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27].O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1>N1C=CC=CC=1>[C:26]([CH2:25][CH2:24][CH2:23][CH2:22][C:21]([C@@:1]1([N:10]2[C:20]3[N:19]=[C:17]([NH2:18])[NH:16][C:14](=[O:15])[C:13]=3[N:12]=[CH:11]2)[O:9][C@H:6]([CH2:7][OH:8])[C@@H:4]([OH:5])[C@H:2]1[OH:3])=[O:29])([OH:28])=[O:27]

Participants

5

Reactant 3

HCID 196Adipic AcidHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 135398635Guanosine

Product 1

HCID 136333635HCID 136333635, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 500 mg of guanosine in anhydrous pyridine was added adipic acid (5 mol eq) and bis(2-oxo-3-oxazolidinyl)-phosphinic chloride (BOPDC) (1.0 mol eq.). The mixture was allowed to stir at room temperature for 18 h, then the solvent was removed in vacuo. The residue was added to 100 mL of ice-cooled water and the aqueous layer adjusted to pH 3.0 and then extracted three times with 60 mL of ethyl acetate. The combined extracts are dried over anhydrous magnesium sulfate and evaporated in vacuo. The residue was chromatographed on a silica gel column and eluted with a mixture of chloroformethanol, whereupon the eluate was evaporated in vacuo.

Workup

  1. customthe solvent was removed in vacuo
  2. additionThe residue was added to 100 mL of ice-
  3. temperaturecooled water
  4. extractionextracted three times with 60 mL of ethyl acetate
  5. dry with materialThe combined extracts are dried over anhydrous magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was chromatographed on a silica gel column
  8. washeluted with a mixture of chloroformethanol, whereupon the eluate
  9. customwas evaporated in vacuo

Sources & evidence

ORD record
ord-6acaac453f914281a249b4ce43b772da
Source dataset
uspto-grants-2000_04
Patent number
US06054441

Reaction notes

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