Lithium Hydroxide → HCID 75202236, compound

HRID 1506801Notes

Reaction equation

HRID 1506801 reaction equation
[OH-].[Li+].[Cl:3][C:4]1[CH:5]=[C:6]([NH:10][C:11]2[N:16]=[N:15][C:14]([C:17]3[CH:18]=[C:19]4[C:24](=[CH:25][CH:26]=3)[C:23](=[O:27])[C:22]([CH2:33][C:34]([O:36]C)=[O:35])([CH2:28][C:29]([F:32])([F:31])[F:30])[CH2:21][CH2:20]4)=[CH:13][CH:12]=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[N:16]=[N:15][C:14]([C:17]3[CH:18]=[C:19]4[C:24](=[CH:25][CH:26]=3)[C:23](=[O:27])[C:22]([CH2:33][C:34]([OH:36])=[O:35])([CH2:28][C:29]([F:32])([F:31])[F:30])[CH2:21][CH2:20]4)=[CH:13][CH:12]=2)[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 90152016HCID 90152016, compound

Product 1

HCID 75202236HCID 75202236, compoundYield 80.8%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

Lithium hydroxide (0.063 g, 1.49 mmol) was added to a solution of 21E1 (0.15 g, 0.298 mmol) in 6 mL of ethanol-water (3:1) mixture, and the reaction mixture was stirred at room temperature for 4 h. After the solvent was removed in vacuo, the residue was diluted with 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 21 (0.118 g, 78%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 12.6 (bs, 1H), 9.78 (s, 1H), 8.19 (s, 1H), 8.13 (d, J=9.6 Hz, 1H), 8.07-7.95 (m, 3H), 7.58 (d, J=8.0 Hz, 1H), 7.36 (t, J=8.0 Hz, 1H), 7.28 (d, J=9.2 Hz, 1H), 7.03 (d, J=7.6 Hz, 1H), 3.24-2.87 (m, 5H), 2.68 (d, J=15.2 Hz, 1H), 2.34 (d, J=14.4 Hz, 1H), 2.14 (m, 1H). ESI-MS m/z: 490 (M+H)+; HPLC purity: 97%.

Workup

  1. customAfter the solvent was removed in vacuo
  2. additionthe residue was diluted with 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-1b6dc48d685a44448705beb572fc0c5e
Source dataset
uspto-grants-2015_12
Patent number
US09221766B2

Reaction notes

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