Lithium hydroxide, monohydrate → (S)-2-[(5-chloro-2-formyl-4H-chromen-3-ylmethyl)-methyl-amino]-4-methyl-pentanoic acid

HRID 1925885Notes

Reaction equation

HRID 1925885 reaction equation
C[O:2][C:3](=[O:25])[C@@H:4]([N:9]([CH2:11][C:12]1[CH:13]([CH:23]=[O:24])[O:14][C:15]2[C:20]([CH:21]=1)=[C:19]([Cl:22])[CH:18]=[CH:17][CH:16]=2)[CH3:10])[CH2:5][CH:6]([CH3:8])[CH3:7].O.[OH-].[Li+]>O1CCCC1.O>[Cl:22][C:19]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:20]=1[CH2:21][C:12]([CH2:11][N:9]([CH3:10])[C@@H:4]([CH2:5][CH:6]([CH3:7])[CH3:8])[C:3]([OH:25])=[O:2])=[C:13]([CH:23]=[O:24])[O:14]2

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86660535(S)-2-[(5-chloro-2-formyl-2H-chromen-3-ylmethyl)-methyl-amino]-4-methyl-pentanoic acid methyl ester

Product 1

HCID 86660536(S)-2-[(5-chloro-2-formyl-4H-chromen-3-ylmethyl)-methyl-amino]-4-methyl-pentanoic acidYield 93.6%

Reagents, catalysts & solvents 1

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

Procedure

A solution of (S)-2-[(5-chloro-2-formyl-2H-chromen-3-ylmethyl)-methyl-amino]-4-methyl-pentanoic acid methyl ester (2.0 g, 5.71 mmol) and lithium hydroxide monohydrate (0.312 g, 7.40 mmol) was stirred at 25° C. for 2 hours in tetrahydrofuran-water (3:1) mixture (90 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-2-formyl-4H-chromen-3-ylmethyl)-methyl-amino]-4-methyl-pentanoic acid (1.78 g, 93.6%).

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-b08fca6e64b4492485ed65a19202eae4
Source dataset
uspto-grants-2012_05
Patent number
US08178689B2

Reaction notes

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