HCID 86673677, compound → Sinefungin

HRID 2273057Notes

Reaction equation

HRID 2273057 reaction equation
[NH2:1][C@@H:2]([CH2:6][CH2:7][C@H:8]([NH2:30])[CH2:9][C@@H:10]1[C@@H:14]([OH:15])[C@@H:13]([O:16]CC#C)[C@H:12]([N:20]2[CH:28]=[N:27][C:26]3[C:21]2=[N:22][CH:23]=[N:24][C:25]=3[NH2:29])[O:11]1)[C:3]([OH:5])=[O:4]>CO.O.CC(O)=O>[CH:23]1[N:24]=[C:25]([NH2:29])[C:26]2[N:27]=[CH:28][N:20]([C@@H:12]3[O:11][C@H:10]([CH2:9][C@@H:8]([NH2:30])[CH2:7][CH2:6][C@H:2]([NH2:1])[C:3]([OH:5])=[O:4])[C@@H:14]([OH:15])[C@H:13]3[OH:16])[C:21]=2[N:22]=1

Participants

3

Reactant 1

HCID 86673677HCID 86673677, compound

Product 1

HCID 65482Sinefungin

Reagents, catalysts & solvents 1

HCID 86607755Acetic acid methanol waterSolvent2×

Procedure

The title detection analyte compound was prepared from Compound 7 (Example 1, Step 3a) by coupling with 6-carboxyfluorescein-PEG3 azide (Berry & Associates, CAS #412319-45-0, Catalog No. FF6110) using the click chemistry methods reported herein; LC/MS (Gemini C18, 3μ, 2.0×50 mm, 400 μL/min, A: 90/10/0.01 H2O/MeOH/HOAc, B 90/10/0.01 MeOH/H2O/HOAc 0-6 min 0-100% B, 6-9 hold at 100% B, 9.1-15 min re-equilibrate at 0% B) 4.3 min (100% purity), ESI+ m/z 498 (z=2; expected molecular mass: 996).

Workup

  1. customat 100% B, 9.1-15 min
  2. custom4.3 min (100% purity), ESI+ m/z 498

Sources & evidence

ORD record
ord-e24faff8ed3342299e1b5a973f3dd869
Source dataset
uspto-grants-2015_09
Patent number
US09120820B2

Reaction notes

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