HCID 69508390, compound → HCID 10429577, compound

HRID 1375668Notes

Reaction equation

HRID 1375668 reaction equation
C[O:2][C:3]([C:5]1[CH:9]=[C:8]([C:10]2[CH:11]=[C:12]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([C:22]4[O:26][N:25]=[C:24]([C:27]([O:29]C)=[O:28])[CH:23]=4)[CH:17]=3)[CH:13]=[CH:14][CH:15]=2)[O:7][N:6]=1)=[O:4]>[OH-].[Na+].CO.O>[C:3]([C:5]1[CH:9]=[C:8]([C:10]2[CH:11]=[C:12]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([C:22]4[O:26][N:25]=[C:24]([C:27]([OH:29])=[O:28])[CH:23]=4)[CH:17]=3)[CH:13]=[CH:14][CH:15]=2)[O:7][N:6]=1)([OH:4])=[O:2]

Participants

4

Reactant 1

HCID 69508390HCID 69508390, compound

Product 1

HCID 10429577HCID 10429577, compoundYield 36.5%

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

The ester from Example 10C (65 mg, 0.16 mmol) was dissolved in 4M NaOH (5 mL) in MeOH/H2O (5:3). After 2 hours no starting material was visible by TLC. When the reaction mixture was acidified to pH 1, the product precipitated out. The titled compound (22 mg, 36%) was obtained after reverse phase HPLC (0–70% acetonitrile in 0.1% aqueous TFA) as a white solid. MS (DEI) positive ion; m/z 376 (M)+: negative ion; m/z 751.1 (2M−H)−, 375.1 (M−H)−. 1H NMR (300 MHz, DMSO-d6) δ 7.6 (s, 2H), 7.7 (t, J=7.8 Hz, 2H), 8.0 (dd, J=8.1, 1.5 Hz, 4H), 8.3 (s, 2H), 14.0 (br s, 2H).

Workup

  1. customthe product precipitated out

Sources & evidence

ORD record
ord-e7bb8ced963c4921bf28723bed887805
Source dataset
uspto-grants-2007_01
Patent number
US07169797B2

Reaction notes

Loading…