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Lithium hydroxide, monohydrate → (S)-2-(8-chloro-3-oxo-3,9-dihydro-1H-chromeno[2,3-c]pyrrol-2-yl)-3-cyclohexyl-propionic acid

HRID 1925880
Notes
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Reaction equation

HRID 1925880 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[C:19]([Cl:25])=[CH:20][CH:21]=[CH:22][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:19]1[C:18]2[CH2:17][C:15]3[CH2:16][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])[C:13](=[O:26])[C:14]=3[O:24][C:23]=2[CH:22]=[CH:21][CH:20]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 67520933(S)-2-(8-chloro-3-oxo-3,3a-dihydro-1H-chromeno[2,3-c]pyrrol-2-yl)-3-cyclohexyl-propionic acid methyl ester

Product 1

HCID 67520747(S)-2-(8-chloro-3-oxo-3,9-dihydro-1H-chromeno[2,3-c]pyrrol-2-yl)-3-cyclohexyl-propionic acidYield 83.3%

Reagents, catalysts & solvents 1

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

Procedure

A solution of (S)-2-(8-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-(8-chloro-3-oxo-3,9-dihydro-1H-chromeno[2,3-c]pyrrol-2-yl)-3-cyclohexyl-propionic acid (1.2 g, 83.3%).

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-b189fad1e1f340dfb1683e2c38f9fe7d
Source dataset
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08178689B2

Reaction notes

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