Sodium Acetate → HCID 178476932, compound

HRID 1364015Notes

Reaction equation

HRID 1364015 reaction equation
[C:1]([NH:4][C@@H:5]1[C@@H:10]([NH:11][C:12]([NH:21]C(OC(C)(C)C)=O)=[N:13]C(OC(C)(C)C)=O)[CH2:9][C:8]([P:29]([O:34]CC)(=[O:33])[O:30][CH2:31][CH3:32])=[CH:7][C@H:6]1[O:37][CH:38]([CH2:41][CH3:42])[CH2:39][CH3:40])(=[O:3])[CH3:2].C([O-])(=O)C.[Na+]>C(O)C>[NH4+:4].[C:1]([NH:4][C@@H:5]1[C@@H:10]([NH:11][C:12]([NH2:21])=[NH:13])[CH2:9][C:8]([P:29]([O:30][CH2:31][CH3:32])(=[O:33])[O-:34])=[CH:7][C@H:6]1[O:37][CH:38]([CH2:41][CH3:42])[CH2:39][CH3:40])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 178476969HCID 178476969, compound

Product 1

HCID 178476932HCID 178476932, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of diethyl ester 12b (2.73 g, 4 mmol) in ethanol (60 mL) was treated with sodium ethanoate in ethanol (6 mmol, 6 mL of 1 M solution) under a nitrogen atmosphere. The mixture was stirred for 18 h at room temperature, and then acidified with Amberlite IR-120 (H+-form). The heterogeneous solution was stirred at 40° C. for 3 h, filtered and concentrated in vacuo. The residual oil was taken up in water (15 mL) and subjected to lyophilization. The residual colorless solids were washed with cold acetone (20 mL×3), dissolved in aqueous NH4HCO3 (15 mL of 0.1 M solution), stirred for 1 h at room temperature, and then lyophilization to afford ammonium salt 13c of Tamiphosphor guanidine monoester (1.22 g, 75%) as white solids.

Workup

  1. stirringThe heterogeneous solution was stirred at 40° C. for 3 h
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. washThe residual colorless solids were washed with cold acetone (20 mL×3)
  5. dissolutiondissolved in aqueous NH4HCO3 (15 mL of 0.1 M solution)
  6. stirringstirred for 1 h at room temperature

Sources & evidence

ORD record
ord-6d24f4e7f30d4879b852bf0938122648
Source dataset
uspto-grants-2011_02
Patent number
US07888337B2

Reaction notes

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