Lithium hydroxide, monohydrate → HCID 67479165, compound

HRID 1019656Notes

Reaction equation

HRID 1019656 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:13][C:14]2[N:19]=[C:18]([N:20]3[CH2:25][CH2:24][CH2:23][C@H:22]([C:26]([NH:28][CH2:29][C:30]4[CH:31]=[C:32]([CH:37]=[CH:38][CH:39]=4)[C:33]([O:35]C)=[O:34])=[O:27])[CH2:21]3)[CH:17]=[CH:16][N:15]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].O.[OH-].[Li+]>O1CCOCC1.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:13][C:14]2[N:19]=[C:18]([N:20]3[CH2:25][CH2:24][CH2:23][C@H:22]([C:26]([NH:28][CH2:29][C:30]4[CH:31]=[C:32]([CH:37]=[CH:38][CH:39]=4)[C:33]([OH:35])=[O:34])=[O:27])[CH2:21]3)[CH:17]=[CH:16][N:15]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 57325613HCID 57325613, compound

Product 1

HCID 67479165HCID 67479165, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 6 (353.7 mg, 0.660 mmol) in a mixture of dioxane (3302 μL) and water (3302 μL) was added lithium hydroxide monohydrate (27.7 mg, 0.660 mmol). The reaction was stirred at room temperature for 72 hours. The reaction mixture was then extracted with DCM. The aqueous layer was diluted with 1N HCl. A precipitate was formed and separated by filtration to give 7 as a light purple solid. 1H NMR (400 MHz, CDCl3 with 1% TFA) δ ppm 1.50-1.70 (m, 1H) 1.83-2.00 (m, 2H) 2.00-2.13 (m, 1H) 2.43-2.56 (m, 1H) 3.23-3.30 (m, 1H) 3.50-3.61 (m, 1H) 3.78-3.92 (m, 10H) 4.01 (d, J=14.08 Hz, 1H) 4.45 (d, J=10.76 Hz, 2H) 6.25-6.37 (m, 1H) 6.86 (s, 2H) 7.38-7.51 (m, 2H) 7.69 (d, J=7.43 Hz, 1H) 7.89-7.99 (m, 2H); M+H 522.23432.

Workup

  1. extractionThe reaction mixture was then extracted with DCM
  2. additionThe aqueous layer was diluted with 1N HCl
  3. customA precipitate was formed
  4. customseparated by filtration

Sources & evidence

ORD record
ord-3c3a14da170242f6a3e9a5d081d141f1
Source dataset
uspto-grants-2014_05
Patent number
US08716281B2

Reaction notes

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