Lithium hydroxide, monohydrate → 3-[4-({[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-[2-(1H-indol-3-yl)ethyl]-amino}-methyl)-phenyl]-acrylic acid

HRID 416209Notes

Reaction equation

HRID 416209 reaction equation
[C:1]([Si:5]([CH3:35])([CH3:34])[O:6][CH2:7][CH2:8][N:9]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([CH:28]=[CH:29][C:30]([O:32]C)=[O:31])=[CH:24][CH:23]=1)[CH2:10][CH2:11][C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[NH:14][CH:13]=1)([CH3:4])([CH3:3])[CH3:2].O[Li].O>C1COCC1.O>[C:1]([Si:5]([CH3:35])([CH3:34])[O:6][CH2:7][CH2:8][N:9]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([CH:28]=[CH:29][C:30]([OH:32])=[O:31])=[CH:24][CH:23]=1)[CH2:10][CH2:11][C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[NH:14][CH:13]=1)([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59036876Methyl 3-[4-({[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-[2-(1H-indol-3-yl)-ethyl]-amino}-methyl)-phenyl]-acrylate

Product 1

HCID 666223893-[4-({[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-[2-(1H-indol-3-yl)ethyl]-amino}-methyl)-phenyl]-acrylic acidYield 79%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of compound 3 (3.18 g, 6.45 mmol) in THF (40 mL) was added a solution of LiOH.H2O (677 mg, 16.14 mmol) in water (20 mL) at room temperature. After 24 h the reaction mixture was concentrated, diluted with water and acidified with 1N HCl until a pH 5-6. A precipitate was formed which was separated by filtration, rinsed with water and dried to afford the title compound 4 (2.43 g, 5.08 mmol, 79% yield) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ(ppm): 12.34 (bs, 1H), 10.75 (s, 1H), 7.63 (d, J=8.2 Hz, 2H), 7.59 (d, J=15.8 Hz, 1H), 7.44-7.35 (m, 3H), 7.32 (d, J=8.0 Hz, 1H), 7.11 (d, J=2.3 Hz, 1H), 7.05 (td, J=7.5, 1.0 Hz, 1H), 6.92 (td, J=7.4, 0.9 Hz, 1H), 6.51 (d, J=15.8 Hz, 1H), 3.79 (s, 2H), 3.69 (t, J=6.4 Hz, 2H), 2.93-2.74 (m, 4H), 2.69 (t, J=6.2 Hz, 2H), 0.88 (s, 9H), 0.05 (s, 6H).

Workup

  1. concentrationAfter 24 h the reaction mixture was concentrated
  2. additiondiluted with water
  3. customA precipitate was formed which
  4. customwas separated by filtration
  5. washrinsed with water
  6. customdried

Sources & evidence

ORD record
ord-bbf862fa92c24dad85bf4a6a1fdffc11
Source dataset
uspto-grants-2012_01
Patent number
US08088805B2

Reaction notes

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