Lithium Hydroxide → HCID 75201399, compound

HRID 1506806Notes

Reaction equation

HRID 1506806 reaction equation
[OH-].[Li+].[Cl:3][C:4]1[CH:5]=[C:6]([NH:10][C:11]2[S:12][C:13]([C:16]3[CH:17]=[C:18]4[C:23](=[CH:24][CH:25]=3)[C:22](=[O:26])[C:21]([CH2:32][C:33]([O:35]C)=[O:34])([CH2:27][C:28]([F:31])([F:30])[F:29])[CH2:20][CH2:19]4)=[CH:14][N:15]=2)[CH:7]=[CH:8][CH:9]=1>C(O)C.O>[Cl:3][C:4]1[CH:5]=[C:6]([NH:10][C:11]2[S:12][C:13]([C:16]3[CH:17]=[C:18]4[C:23](=[CH:24][CH:25]=3)[C:22](=[O:26])[C:21]([CH2:32][C:33]([OH:35])=[O:34])([CH2:27][C:28]([F:31])([F:30])[F:29])[CH2:20][CH2:19]4)=[CH:14][N:15]=2)[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 90152015HCID 90152015, compound

Product 1

HCID 75201399HCID 75201399, compoundYield 59.9%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

Lithium hydroxide (0.05 g, 1.18 mmol) was added to a solution of 26D2 (0.12 g, 0.236 mmol) in 8 mL of ethanol-water (3:1) mixture, and the reaction mixture was stirred at room temperature for 1 h. After the solvent was removed in vacuo, the residue was dissolved in water. The aqueous layer was acidified by addition of saturated citric acid solution until pH 2 was attained. The resulting solution was cooled to 0° C. and solids obtained were filtered off and dried under vacuum to afford the title compound (0.07 g, 59%) as a yellow solid. 1H NMR (300 MHz, DMSO-d6) δ 10.9 (s, 1H), 7.95 (m, 2H), 7.88 (d, J=8.4 Hz, 1H), 7.56 (d, J=8.1 Hz, 1H), 7.5 (m, 2H), 7.35 (t, J=8.1 Hz, 1H), 7.02 (d, J=8.0 Hz, 1H), 3.14-2.80 (m, 4H), 2.69 (d, J=18.4 Hz, 1H), 2.46-2.31 (m, 2H), 2.12 (m, 1H). ESI-MS m/z: 495 (M+H)+; HPLC purity: 99%

Workup

  1. customAfter the solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in water
  3. additionThe aqueous layer was acidified by addition of saturated citric acid solution until pH 2
  4. temperatureThe resulting solution was cooled to 0° C.
  5. customsolids obtained
  6. filtrationwere filtered off
  7. customdried under vacuum

Sources & evidence

ORD record
ord-4c68c70a2a254cfb86e7d621cf836469
Source dataset
uspto-grants-2015_12
Patent number
US09221766B2

Reaction notes

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