Sodium Hydroxide → HCID 17751582, compound

HRID 643924Notes

Reaction equation

HRID 643924 reaction equation
C[O:2][C:3](=[O:29])[C:4]([CH3:28])([CH3:27])[CH2:5][CH2:6][CH2:7][CH:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([N:19]3[CH2:23][C:22](=[O:24])[NH:21][S:20]3(=[O:26])=[O:25])=[C:13]([OH:18])[CH:14]=2)[CH2:9]1.[OH-].[Na+]>C1COCC1.CO.O>[OH:18][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][C:12]=1[N:19]1[CH2:23][C:22](=[O:24])[NH:21][S:20]1(=[O:26])=[O:25])[CH2:9][CH:8]([CH2:7][CH2:6][CH2:5][C:4]([CH3:28])([CH3:27])[C:3]([OH:29])=[O:2])[CH2:17][CH2:16]2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59263261HCID 59263261, compound

Product 1

HCID 17751582HCID 17751582, compound

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 5-[6-Hydroxy-7-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-1,2,3,4-tetrahydronaphthalen-2-yl]-2,2-dimethylpentanoic acid methyl ester (50 mg, 0.12 mmol) in THF/MeOH/H2O (3:3:1 v/v/v, 1 mL,) is added NaOH (50 mg) and it is heated at 80° C. in microwave for 10 min. The solution is concentrated, dissolved in H2O and neutralized with 1N HCl solution. It is then purified by RP-HPLC to give the title compound as a light yellow solid: 1H NMR(CD3OD) δ1.17 (s, 6H), 1.29-1.35 (m, 5H), 1.39-1.41 (m, 2H), 1.60-1.70 (m, 1H), 1.90-1.94 (m 1H), 2.25-2.35 (m, 1H), 2.71-2.75 (m, 3H), 4.27 (s, 2H), 6.59 (s, 1H), 7.09 (s, 1H); (M−H)−=409.

Workup

  1. concentrationThe solution is concentrated
  2. dissolutiondissolved in H2O and neutralized with 1N HCl solution
  3. customIt is then purified by RP-HPLC

Sources & evidence

ORD record
ord-5dd77a50e6cd4d39a9681db2da27d454
Source dataset
uspto-grants-2010_04
Patent number
US07700633B2

Reaction notes

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