HCID 67604151, compound → HCID 70063386, compound

HRID 2255297Notes

Reaction equation

HRID 2255297 reaction equation
[NH2:1][N:2]=[CH:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:27])[CH2:12][CH2:13][C:14]([NH:16][CH:17]([CH:24]2[CH2:26][CH2:25]2)[CH2:18][C:19]([O:21]CC)=[O:20])=[O:15])=[CH:6][CH:5]=1>P([O-])([O-])([O-])=O>[NH2:1][N:2]=[CH:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:27])[CH2:12][CH2:13][C:14]([NH:16][CH:17]([CH:24]2[CH2:26][CH2:25]2)[CH2:18][C:19]([OH:21])=[O:20])=[O:15])=[CH:6][CH:5]=1

Participants

3

Reactant 1

HCID 67604151HCID 67604151, compound

Product 1

HCID 70063386HCID 70063386, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 1061PhosphateSolvent

Procedure

Porcine liver esterase (200 μL, Sigma, 11 mg/mL in 3.2 M (NH4)2SO4 at pH=8) was added to the final product of Example 28 in 20mL of 0.1 M phosphate buffer (pH=7.4). After 20 h at 23° C., the reaction mixture was concentrated in vacuo. The residue was dissolved in 1N HCl (3 mL) and subsequently diluted with acetonitrile (5 mL) followed by immediate purification by reverse phase HPLC using the conditions of Example 1 to afford 23.0 mg (83%) of the title compound. The product was verified by 13C NMR (CD3OD) δ 1.8, 2.6, 15.0, 30.3, 31.8, 39.1, 50.6, 119.2, 122.1, 128.6, 144.3, 166.8, 172.0, 172.4, 173.4; Fast Atom Bombardment mass spectrometry (MH+)=347.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved in 1N HCl (3 mL)
  3. additionsubsequently diluted with acetonitrile (5 mL)
  4. customfollowed by immediate purification by reverse phase HPLC

Sources & evidence

ORD record
ord-893eb25be69542d5b667007fcc4b23f9
Source dataset
uspto-grants-1993_08
Patent number
US05239113

Reaction notes

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