Lithium Hydroxide → HCID 58989765, compound

HRID 1663156Notes

Reaction equation

HRID 1663156 reaction equation
C[O:2][C:3](=[O:29])[C:4]1[CH:9]=[C:8]([CH2:10][NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18](=[O:27])[NH:19][O:20][CH2:21][CH:22]2[CH2:26][CH2:25][CH2:24][CH2:23]2)[CH:7]=[CH:6][C:5]=1[F:28].[OH-].[Li+]>C1COCC1.O>[CH:22]1([CH2:21][O:20][NH:19][C:18]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[NH:11][CH2:10][C:8]2[CH:7]=[CH:6][C:5]([F:28])=[C:4]([CH:9]=2)[C:3]([OH:29])=[O:2])=[O:27])[CH2:23][CH2:24][CH2:25][CH2:26]1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 58989927HCID 58989927, compound

Product 1

HCID 58989765HCID 58989765, compoundYield 77.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

5-[(2-Cyclopentylmethoxycarbamoyl-phenylamino)-methyl]-2-fluoro-benzoic acid methyl ester (Example 493, 511 mg) was dissolved in THF (15 ml) and water (5 ml). Lithium hydroxide (122 mg) was added and the mixture was heated to 60° C. The reaction mixture was stirred at this temperature for 15 hours, cooled to room temperature and concentrated under reduced pressure. The residue was diluted with water and 1M hydrochloric acid was added until a precipitate formed. The solid material was isolated by filtration and washed with water and dried under high vacuum and gave the title compound (380 mg) as a white powder. 13C-NMR (DMSO-d6) δ 166.9, 165.0, 160.0, 148.4, 135.9, 133.0, 132.4, 130.1, 128.0, 119.1, 116.9, 114.6, 113.4, 111.5, 79.4, 44.8, 37.6, 28.9, 24.9.

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue was diluted with water and 1M hydrochloric acid
  4. additionwas added until a precipitate
  5. customformed
  6. customThe solid material was isolated by filtration
  7. washwashed with water
  8. customdried under high vacuum

Sources & evidence

ORD record
ord-52512b5c14554f55bc671effa5129080
Source dataset
uspto-grants-2011_10
Patent number
US08034811B2

Reaction notes

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