HCID 86758589, compound → HCID 86758587, compound

HRID 1016272Notes

Reaction equation

HRID 1016272 reaction equation
[N:1]([C@@H:4]1[C@@H:8]([CH2:9][OH:10])[O:7][C@@H:6]([N:11]2[CH:19]=[C:17]([CH3:18])[C:15](=[O:16])[NH:14][C:12]2=[O:13])[CH2:5]1)=[N+:2]=[N-:3].CO[CH2:22][CH:23]([CH3:34])[CH2:24][C@@H:25]([C:27]([O:29][P:30]([NH2:33])(=[O:32])[O-:31])=[O:28])[NH2:26]>CN.CO>[N:1]([C@@H:4]1[C@@H:8]([CH2:9][OH:10])[O:7][C@@H:6]([N:11]2[CH:19]=[C:17]([CH3:18])[C:15](=[O:16])[NH:14][C:12]2=[O:13])[CH2:5]1)=[N+:2]=[N-:3].[CH3:4][NH:1][CH2:22][CH:23]([CH3:34])[CH2:24][C@@H:25]([C:27]([O:29][P:30]([NH2:33])(=[O:32])[O-:31])=[O:28])[NH2:26]

Participants

4

Reactant 1

HCID 86758589HCID 86758589, compound

Product 1

HCID 86758587HCID 86758587, compoundYield 131.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6329MethylamineSolvent

Procedure

Compound 21 (38 mg) was dissolved in 2 mL of 10 M methyl amine in methanol and stirred in a sealed vial for 50 d. The reaction mixture was then concentrated under reduced pressure. Flash chromatography (SiO2, 5:2:0.25 CHCl3/MeOH/H2O containing 0.5% conc. NH4OH) gave the desired product (25 mg) was awhite solid. 1H NMR (D2O, 300 MHz) 7.588 (d, J=1.1 Hz, 1H), 6.081 (t, J=6.8 Hz, 1H), 4.275 (m, 1H), 3.995 (m, 1H), 3.896-3.746 (m, 2H), 3.403 (m, 1H), 2.570 (s, 3H), 2.320 (m, 2H), 1.753 (d, J=1.1 Hz, 3H), 1.504 (m, 1H), 1.352-1.225 (m, 2H), 0.693 (d, J=6.6 Hz, 6H); 31P NMR (D2O, 121 MHz) 6.359.

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure

Sources & evidence

ORD record
ord-5be416710af24c6b817fd87af6ea179e
Source dataset
uspto-grants-2002_11
Patent number
US06475985B1

Reaction notes

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