HCID 59289323, compound → HCID 59289358, compound

HRID 2191056Notes

Reaction equation

HRID 2191056 reaction equation
[N:1]([C@@:4]1(/[CH:29]=[CH:30]/[P:31](=[O:34])([OH:33])[OH:32])[C@@H:8]([OH:9])[C@@H:7]([OH:10])[C@H:6]([N:11]2[CH:19]=[N:18][C:17]3[C:12]2=[N:13][CH:14]=[N:15][C:16]=3[NH:20]C(=O)C2C=CC=CC=2)[O:5]1)=[N+:2]=[N-:3]>[NH4+].[OH-]>[NH2:20][C:16]1[N:15]=[CH:14][N:13]=[C:12]2[C:17]=1[N:18]=[CH:19][N:11]2[C@@H:6]1[O:5][C@@:4](/[CH:29]=[CH:30]/[P:31](=[O:32])([OH:34])[OH:33])([N:1]=[N+:2]=[N-:3])[C@@H:8]([OH:9])[C@H:7]1[OH:10]

Participants

3

Reactant 1

HCID 59289323HCID 59289323, compound

Product 1

HCID 59289358HCID 59289358, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 14923Ammonium HydroxideSolvent

Procedure

Compound 36.6 (crude 233 mg) was dissovled in 10 mL concentrated NH4OH. The solution was stirred at r.t. for 24 h and then concentrated under reduced pressure. The residue was subjected to a reverse phase HPLC eluting with 0-15% CH3CN in water to give compound 36.7 (40 mg, 22% yield). 1H NMR (D2O, 300 MHz) 8.12 (s, 1H), 8.03 (s, 1H), 6.14 (br m, 3H), 4.66 (m, 1H), 4.40 (d, J=6.0 Hz, 1H),; 31P NMR (D2O 121.4 MHz) 7.1; MS (ESI) m/z 385 [M+H]+.

Workup

  1. concentrationconcentrated under reduced pressure
  2. washeluting with 0-15% CH3CN in water

Sources & evidence

ORD record
ord-f6b999f0a5284841b5da85014caacc81
Source dataset
uspto-grants-2012_12
Patent number
US08324179B2

Reaction notes

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