Lithium hydroxide, monohydrate → HCID 57546162, compound

HRID 913921Notes

Reaction equation

HRID 913921 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([CH:11]([O:16][CH2:17][C:18]2([C:31]3[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=3)[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]2)[C:12]([O:14]C)=[O:13])[C:8]2[C:4](=[CH:5][N:6]([CH2:38][O:39][CH2:40][CH2:41][Si:42]([CH3:45])([CH3:44])[CH3:43])[N:7]=2)[CH:3]=1.O.[OH-].[Li+]>O1CCCC1.CO.O>[C:27]([O:26][C:24]([N:21]1[CH2:22][CH2:23][C:18]([CH2:17][O:16][CH:11]([C:9]2[C:8]3[C:4](=[CH:5][N:6]([CH2:38][O:39][CH2:40][CH2:41][Si:42]([CH3:43])([CH3:44])[CH3:45])[N:7]=3)[CH:3]=[C:2]([Cl:1])[CH:10]=2)[C:12]([OH:14])=[O:13])([C:31]2[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=2)[CH2:19][CH2:20]1)=[O:25])([CH3:30])([CH3:29])[CH3:28]

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 57546118HCID 57546118, compound

Product 1

HCID 57546162HCID 57546162, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 4-((1-(5-chloro-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-7-yl)-2-methoxy-2-oxoethoxy)methyl)-4-(4-fluorophenyl)piperidine-1-carboxylate (150 mg, 0.226 mmol) in tetrahydrofuran (1 mL) and methanol (1 mL) at 0° C. was added a solution of lithium hydroxide monohydrate (28.5 mg, 0.679 mmol) in water (0.5 mL). After 1 h, the reaction was concentrated to remove most of the solvent. The resulting residue was dissolved in a minimum of water, and acidified with 1N hydrochloric acid to give a white solid which was collected by filtration. 1H-NMR (CDCl3, 500 MHz) δ 8.83 (bs, 1H), 8.05 (s, 1H), 7.59 (d, J=1.8 Hz, 1H), 7.28 (dd, J=8.9, 5.5 Hz, 2H), 7.10 (s, 1H), 6.98 (dd, J=8.9, 8.6 Hz, 2H), 5.65 (s, 2H), 5.23 (s, 1H), 3.62-3.82 (m, 3H), 3.58 (t, J=8.2 Hz, 2H), 3.37 (d, J=8.9 Hz, 1H), 3.02 (m, 2H), 2.17 (m, 1H), 2.08 (m, 1H), 1.92 (m, 1H), 1.84 (m, 1H), 1.41 (s, 9H), 0.91 (m, 2H), −0.05 (s, 9H); 13C NMR (126 MHz, CDCl3) δ ppm 170.7, 161.5 (d, J=246 Hz), 155.1, 145.3, 138.1, 128.9 (d, J=7.7 Hz), 128.2, 126.5, 126.4, 123.3, 122.7, 119.9, 115.3 (d, J=20.2 Hz), 82.0, 79.7, 78.7, 77.7, 68.0, 41.3, 39.8, 32.1, 31.9, 28.5, 17.9, −1.4.

Workup

  1. concentrationthe reaction was concentrated
  2. customto remove most of the solvent
  3. dissolutionThe resulting residue was dissolved in a minimum of water
  4. customto give a white solid which
  5. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-42c90deb9db7407686e3a50bef35adbb
Source dataset
uspto-grants-2011_09
Patent number
US08026257B2

Reaction notes

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