Lithium hydroxide, monohydrate → HCID 59038469, compound

HRID 1058402Notes

Reaction equation

HRID 1058402 reaction equation
C[O:2][C:3](=[O:26])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([NH:12][C@@H:13]([C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17][CH:16]=2)[CH3:14])=[O:11])=[CH:6][C:5]=1[Cl:25].O.[OH-].[Li+]>O1CCCC1.CO.O>[Cl:25][C:5]1[CH:6]=[C:7]([C:10]([NH:12][C@@H:13]([C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17][CH:16]=2)[CH3:14])=[O:11])[CH:8]=[CH:9][C:4]=1[C:3]([OH:26])=[O:2]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59038461HCID 59038461, compound

Product 1

HCID 59038469HCID 59038469, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a solution of (R)-2-chloro-4-[[1-(naphthalen-1-yl)ethylamino]carbonyl]benzoic acid methyl ester (Example 82; 3.00 g, ˜8.5 mmol) in tetrahydrofuran/methanol/water (3:1:1; 20 mL) was added lithium hydroxide monohydrate (1.43 g, 34 mmol). The mixture was allowed to stir at room temperature for 4 h and then concentrated in vacuo to remove tetrahydrofuran and methanol. The concentrate was diluted with water and extracted with three portions of ethyl acetate. The organic extracts were discarded and the aqueous layer was acidified with 1N hydrochloric acid solution. Ethyl acetate was added and the resulting colorless solid was recovered by filtration and washed with ethyl acetate. The layers in the filtrate were separated and the organic phase was dried (MgSO4), filtered and concentrated. The resulting residue was combined with the previously recovered solid to give (R)-2-chloro-4-[[1-(naphthalen-1-yl)ethylamino]carbonyl]benzoic acid (2.42 g, 84% yield).

Workup

  1. concentrationconcentrated in vacuo
  2. customto remove tetrahydrofuran and methanol
  3. additionThe concentrate was diluted with water
  4. extractionextracted with three portions of ethyl acetate
  5. additionEthyl acetate was added
  6. filtrationthe resulting colorless solid was recovered by filtration
  7. washwashed with ethyl acetate
  8. customThe layers in the filtrate were separated
  9. dry with materialthe organic phase was dried (MgSO4)
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-f075c80ca86046cf823b6041e4444f4a
Source dataset
uspto-grants-2003_02
Patent number
US06515124B2

Reaction notes

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