Potassium Hydroxide → HCID 59263269, compound

HRID 643876Notes

Reaction equation

HRID 643876 reaction equation
C([O:3][C:4](=[O:28])[CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][C:13]([N:20]3[CH2:24][C:23](=[O:25])[NH:22][S:21]3(=[O:27])=[O:26])=[C:14]([OH:19])[CH:15]=2)[CH:10]=1)C.[OH-].[K+]>CO.O>[OH:19][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][C:13]=1[N:20]1[CH2:24][C:23](=[O:25])[NH:22][S:21]1(=[O:27])=[O:26])[CH:10]=[C:9]([CH2:8][CH2:7][CH2:6][CH2:5][C:4]([OH:28])=[O:3])[CH:18]=[CH:17]2

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 59263265HCID 59263265, compound

Product 1

HCID 59263269HCID 59263269, compound

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Conditions

Temperature
50 °C

Procedure

To a solution of 5-[6-hydroxy-7-(1,1,4-trioxo-[1,2,5]thiadiazolidin-2-yl)-naphthalen-2-yl]-pentanoic acid ethyl ester (Example 8, 0.025 g, 0.053 mmol) in MeOH/H2O (3 mL) is added KOH (0.009 g, 0.159 mmol). This is stirred at 50° C. for 18 h. LC/MS reveals the desired product, so the reaction solution is acidified using 1 N HCl, extracted with EtOAc. The organic layer is washed with brine, dried over MgSO4, filtered, and concentrated in vacuo to afford 5-[6-hydroxy-7-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-naphthalen-2-yl]-pentanoic acid as a white solid: 1H NMR (MeOD) δ7.88 (s, 1H), 7.59 (d, J=8.0 Hz, 1H), 7.54 (s, 1H), 7.31 (dd, J=8.46, 1.64 Hz, 1H), 7.21 (s, 1H), 4.61 (s, 2H), 2.75 (t, J=7.33 Hz, 2H), 2.32 (t, J=7.07 Hz, 2H), 1.61 (m, 4H). Retention time=0.87 min (Method A); (M−H)−=377.

Sources & evidence

ORD record
ord-a26ab9b60fe5478e9ec2eb1b0fc771e7
Source dataset
uspto-grants-2010_04
Patent number
US07700633B2

Reaction notes

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