Lithium Hydroxide → HCID 57595387, compound

HRID 1786055Notes

Reaction equation

HRID 1786055 reaction equation
C[O:2][C:3](=[O:42])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]([N:20]3[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[C@H:23]([N:30]([C:38](=[O:40])[CH3:39])[C:31]4[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=4)[CH2:22][C@@H:21]3[CH3:41])=[O:19])=[CH:14][CH:13]=2)[CH:5]=1.[Li+].[OH-]>CO.C1COCC1>[C:38]([N:30]([C:31]1[CH:32]=[CH:33][C:34]([Cl:37])=[CH:35][CH:36]=1)[C@H:23]1[C:24]2[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:20]([C:18]([C:15]2[CH:16]=[CH:17][C:12]([O:11][CH2:10][C:6]3[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=3)[C:3]([OH:42])=[O:2])=[CH:13][CH:14]=2)=[O:19])[C@@H:21]([CH3:41])[CH2:22]1)(=[O:40])[CH3:39]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 57595415HCID 57595415, compound

Product 1

HCID 57595387HCID 57595387, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

(2S,4R)-3-(4-{4-[Acetyl-(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenoxymethyl)-benzoic acid methyl ester (93 mg, 0.16 mmol) was dissolved in MeOH/THF (2:1, 3 mL). To this solution was added LiOH (2M in H2O, 2 mL). The reaction was stirred at room temperature for 18 hours. The reaction mixture was concentrated in vacuo to remove MeOH and THF. Then 6N HCl aqueous solution was added to acidify the reaction mixture to pH 2-3. The reaction mixture was extracted with DCM (5 mL×3). The extract was washed with water (15 mL), brine (15 mL) and dried over MgSO4, filtered and concentrated under reduced pressure. The crude residue was purified by preparatory HPLC to afford the product (90 mg, 100%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customto remove MeOH and THF
  3. additionThen 6N HCl aqueous solution was added
  4. extractionThe reaction mixture was extracted with DCM (5 mL×3)
  5. washThe extract was washed with water (15 mL), brine (15 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe crude residue was purified by preparatory HPLC

Sources & evidence

ORD record
ord-a5ea1284cdf642f9a09944db69b01634
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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