Sodium Hydroxide → HCID 24883358, compound

HRID 2103316Notes

Reaction equation

HRID 2103316 reaction equation
C[O:2][C:3](=[O:26])[CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([O:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:15][CH:14]=2)[CH2:8][CH2:7]1.[OH-].[Na+]>CO.O>[O:19]([C:16]1[CH:15]=[CH:14][C:13]([O:12][CH:9]2[CH2:10][CH2:11][N:6]([CH2:5][CH2:4][C:3]([OH:26])=[O:2])[CH2:7][CH2:8]2)=[CH:18][CH:17]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69003367HCID 69003367, compound

Product 1

HCID 24883358HCID 24883358, compoundYield 113.5%

Reagents, catalysts & solvents 1

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

Conditions

Temperature
50 °C

Procedure

To a solution of the product (143 mg, 0.4 mmol) from step 1 in 4:1 mixture of MeOH/water (2 mL) was added 2M solution of NaOH (241 uL, 0.48 mmol). Reaction mixture was heated at 50° C. for 16 h. Solvent was removed in vacuo, residue was washed with water, dissolved in MeOH and filtered. Filtrate was concentrated to give the product as white solid (155 mg, 100%): MS; m/z 342.5 (M+H); 1H NMR (400 MHz, DMSO-d6); δ 1.99 (br, 2H), 2.17-2.21 (m, 2H), 2.84-2.88 (m, 2H), 3.25-3.32 (m, 7H), 6.92-7.10 (m, 7H), 7.33-7.37 (m, 2H); HPLC (UV); 93%.

Workup

  1. customReaction mixture
  2. customSolvent was removed in vacuo, residue
  3. washwas washed with water
  4. dissolutiondissolved in MeOH
  5. filtrationfiltered
  6. concentrationFiltrate was concentrated

Sources & evidence

ORD record
ord-231c3cf5cb4f4c6ab2cacc8a3c49ebd8
Source dataset
uspto-grants-2009_08
Patent number
US07576102B2

Reaction notes

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