Water → HCID 46829808, compound

HRID 400777Notes

Reaction equation

HRID 400777 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[C:8]([C:12]([O:14]CC)=[O:13])[NH:9]2)=[CH:5][C:4]=1[C:17]1[N:21]=[C:20]([C:22]2[CH:27]=[CH:26][C:25]([N:28]3[CH2:33][CH2:32][CH2:31][CH2:30][CH:29]3[CH3:34])=[C:24]([C:35]([F:38])([F:37])[F:36])[CH:23]=2)[O:19][N:18]=1.[OH-].[Li+].O>C1COCC1.[OH-].[Na+]>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[C:8]([C:12]([OH:14])=[O:13])[NH:9]2)=[CH:5][C:4]=1[C:17]1[N:21]=[C:20]([C:22]2[CH:27]=[CH:26][C:25]([N:28]3[CH2:33][CH2:32][CH2:31][CH2:30][CH:29]3[CH3:34])=[C:24]([C:35]([F:38])([F:37])[F:36])[CH:23]=2)[O:19][N:18]=1

Participants

6

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 46829807HCID 46829807, compound

Product 1

HCID 46829808HCID 46829808, compoundYield 86.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of example 20 (71 mg; 0.13 mmol) in THF (4.5 mL) was added lithium hydroxide (16 mg; 0.67 mmol) (1.50 ml), followed by water (2 mL) and the resulting mixture was stirred at RT for 24 hours. The solution was diluted with NaOH (0.1 M) washed with Et2O and acidified to pH 1 with 1M HCl (1 M). The formed precipitate was filtered, washed with water and dried under high vacuum to give the title compound as an off-white solid (56 mg, 83%). 1H NMR (DMSO-d6) δ 12.97 (bs, 1H), 11.86 (bs, 1H), 8.45-8.41 (m, 1H), 8.37-8.36 (m, 1H), 8.31 (s, 1H), 7.85 (d, J=8.4 Hz, 1H), 7.20 (m, 1H), 7.06 (m, 1H), 3.90 (s, 1H), 3.15 (m, 1H), 2.97-2.93 (m, 1H), 2.64-2.57 (m, 1H), 1.80-1.76 (m, 2H), 1.63-1.29 (m, 4H), 0.78 (d, J=6 Hz, 3H). HPLC (Method A) Rt 5.43 min (Purity: 99.1%). LC/MS (method A): 501.3 (M+H)+.

Workup

  1. washwashed with Et2O
  2. filtrationThe formed precipitate was filtered
  3. washwashed with water
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-fafd8b0b03ca428ebd714dad1f7d3ec5
Source dataset
uspto-grants-2014_06
Patent number
US08741923B2

Reaction notes

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