Lithium hydroxide, monohydrate → HCID 67521062, compound

HRID 1925917Notes

Reaction equation

HRID 1925917 reaction equation
C[O:2][C:3](=[O:27])[C@@H:4]([N:12]1[CH2:16][C:15]2=[CH:17][C:18]3[CH:19]=[CH:20][CH:21]=[C:22]([Cl:25])[C:23]=3[O:24][CH:14]2[C:13]1=[O:26])[CH2:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.O.[OH-].[Li+]>O1CCCC1.O>[Cl:25][C:22]1[C:23]2[O:24][C:14]3[C:13](=[O:26])[N:12]([C@@H:4]([CH2:5][CH:6]4[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]4)[C:3]([OH:27])=[O:2])[CH2:16][C:15]=3[CH2:17][C:18]=2[CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 67521443HCID 67521443, compound

Product 1

HCID 67521062HCID 67521062, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

A solution of (S)-2-(5-chloro-3-oxo-3,3a-dihydro-1H-chromeno[2,3-c]pyrrol-2-yl)-3-cyclohexyl-propionic acid methyl ester (1.5 g, 4.0 mmol) and lithium hydroxide monohydrate (0.22 g, 5.22 mmol) was stirred at 25° C. for 2 hours in tetrahydrofuran-water (3:1) mixture (50 mL). The reaction mixture was concentrated in vacuo to remove tetrahydrofuran, and the residue was acidified with 2N-hydrochloric acid, and diluted with water. The resulting solution was extracted with ethyl acetate (3×). The combined organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed in vacuo to afford (S)-2-(5-chloro-3-oxo-3,9-dihydro-1H-chromeno[2,3-c]pyrrol-2-yl)-3-cyclohexyl-propionic acid (1.2 g, 83.3%) as off white solid.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customto remove tetrahydrofuran
  3. additiondiluted with water
  4. extractionThe resulting solution was extracted with ethyl acetate (3×)
  5. washThe combined organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-1f7a05c21f424a60a8979a5f823e2457
Source dataset
uspto-grants-2012_05
Patent number
US08178689B2

Reaction notes

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