Sodium Hydroxide → HCID 71239373, compound

HRID 1424299Notes

Reaction equation

HRID 1424299 reaction equation
[F:1][C:2]([F:34])([F:33])[CH2:3][CH2:4][CH:5]([C:17]1[CH:32]=[CH:31][C:20]([C:21]([NH:23][CH2:24][CH2:25][C:26]([O:28]CC)=[O:27])=[O:22])=[CH:19][CH:18]=1)[NH:6][C:7]1[CH:8]=[N:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2.[OH-].[Na+]>CO.O1CCCC1>[F:34][C:2]([F:1])([F:33])[CH2:3][CH2:4][CH:5]([C:17]1[CH:32]=[CH:31][C:20]([C:21]([NH:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27])=[O:22])=[CH:19][CH:18]=1)[NH:6][C:7]1[CH:8]=[N:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86718842HCID 86718842, compound

Product 1

HCID 71239373HCID 71239373, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl(+/−)-3-(4-(4,4,4-trifluoro-1-(quinolin-3-ylamino)butyl)benzamido)propanoate (74 mg, 0.16 mmol) in methanol (0.78 mL) and tetrahydrofuran (0.78 mL) was added 1 N aq sodium hydroxide (0.78 mL, 0.78 mmol). After 10 minutes, the solution was concentrated under reduced pressure to remove methanol and tetrahydrofuran. The mixture was then acidified to pH 4 with 1 N aq hydrochloric acid and diluted with sat. aq sodium chloride (10 mL). The aqueous layer was extracted with ethyl acetate (3×15 mL). The combined organic layers were dried over Na2SO4 and filtered, and the filtrate was concentrated under reduced pressure to give (+/−)-3-(4-(4,4,4-trifluoro-1-(quinolin-3-ylamino)butyl)benzamido)propanoic acid. 1HNMR (400 MHz, DMSO-d6) δ 12.18 (br. s., 1H), 8.56 (d, J=2.7 Hz, 1H), 8.44 (t, J=5.6 Hz, 1H), 7.78 (d, J=8.4 Hz, 2H), 7.76-7.72 (m, 1H), 7.54 (d, J=8.2 Hz, 2H), 7.52-7.48 (m, 1H), 7.37-7.27 (m, 2H), 7.03 (d, J=7.8 Hz, 1H), 6.86 (d, J=2.5 Hz, 1H), 4.73-4.61 (m, 1H), 3.46-3.37 (m, 2H), 2.47 (t, J=7.0 Hz, 2H), 2.39-2.23 (m, 1H), 2.14-1.92 (m, 2H), 1.20-1.13 (m, 1H); (M+1): 446.2.

Workup

  1. concentrationthe solution was concentrated under reduced pressure
  2. customto remove methanol and tetrahydrofuran
  3. additiondiluted with sat. aq sodium chloride (10 mL)
  4. extractionThe aqueous layer was extracted with ethyl acetate (3×15 mL)
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-91b41470185144bda1d110a0787f04e8
Source dataset
uspto-grants-2015_01
Patent number
US08927577B2

Reaction notes

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