Tetrabutylammonium Hydroxide → HCID 178525569, compound

HRID 1028202Notes

Reaction equation

HRID 1028202 reaction equation
C[O:2][C:3]([CH2:5][C@H:6]1[CH2:11][CH2:10][C@H:9]([O:12][C:13]([N:15]2[CH2:24][CH2:23][C:22]3[C:17](=[CH:18][CH:19]=[C:20]([NH:25][C:26]([NH:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=4[F:35])=[O:27])[CH:21]=3)[CH2:16]2)=[O:14])[CH2:8][CH2:7]1)=[O:4].[OH-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCOCC1>[C:3]([CH2:5][C@H:6]1[CH2:11][CH2:10][C@H:9]([O:12][C:13]([N:15]2[CH2:24][CH2:23][C:22]3[C:17](=[CH:18][CH:19]=[C:20]([NH:25][C:26]([NH:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=4[F:35])=[O:27])[CH:21]=3)[CH2:16]2)=[O:14])[CH2:8][CH2:7]1)([OH:4])=[O:2]

Participants

4

Reactant 2

HCID 2723671Tetrabutylammonium HydroxideHCID 178500708HCID 178500708, compound

Product 1

HCID 178525569HCID 178525569, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a 1,4-dioxane (20 mL) mixture of trans-6-[3-(2-fluoro-phenyl)-ureido]-3,4-dihydro-1H-isoquinoline-2-carboxylic acid 4-methoxycarbonylmethyl-cyclohexyl ester (1.48 g) obtained in Example 1, tetrabutylammonium hydroxide (1.0 mol/L aqueous solution, 4.0 mL) was added at room temperature. The reaction mixture was stirred for 22 hours and concentrated. The residue was acidified with a 1N aqueous hydrochloric acid solution (30 mL), then diluted with ethyl acetate, and vigorously stirred until complete dissolution. The separated organic layer was washed with saturated brine, then dried over sodium sulfate, and then concentrated. The residue was purified by chromatography (dichloromethane/methanol). The obtained solid was recrystallized (isopropyl alcohol) to obtain the title compound (1.04 g, 72%) as a white solid.

Workup

  1. additionwas added at room temperature
  2. concentrationconcentrated
  3. additiondiluted with ethyl acetate
  4. stirringvigorously stirred until complete dissolution
  5. washThe separated organic layer was washed with saturated brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography (dichloromethane/methanol)
  9. customThe obtained solid was recrystallized (isopropyl alcohol)

Sources & evidence

ORD record
ord-271966f7e9d246729963a43e70a5ad45
Source dataset
uspto-grants-2014_05
Patent number
US08735425B2

Reaction notes

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