Lithium Hydroxide → HCID 178525542, compound

HRID 220142Notes

Reaction equation

HRID 220142 reaction equation
[F:1][C:2]([F:27])([F:26])[C:3]1[NH:7][N:6]=[C:5]([C:8]2[CH:13]=[CH:12][C:11]([C@H:14]3[CH2:19][CH2:18][C@H:17]([CH2:20][C:21]([O:23]CC)=[O:22])[CH2:16][CH2:15]3)=[CH:10][CH:9]=2)[CH:4]=1.[OH-].[Li+]>O1CCCC1>[F:27][C:2]([F:1])([F:26])[C:3]1[NH:7][N:6]=[C:5]([C:8]2[CH:9]=[CH:10][C:11]([C@H:14]3[CH2:15][CH2:16][C@H:17]([CH2:20][C:21]([OH:23])=[O:22])[CH2:18][CH2:19]3)=[CH:12][CH:13]=2)[CH:4]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 178471761HCID 178471761, compound

Product 1

HCID 178525542HCID 178525542, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A round bottom flask was charged with the product from Example 26B (0.520 g, 1.36 mmol) and 6 mL of 20% aqueous tetrahydrofuran. Lithium hydroxide was added (114 mg, 2.72 mmol), and the reaction stirred at room temperature overnight. After 16 hours, the reaction was quenched with 1 N HCl, and the mixture filtered over a bed of celite. Evaporation of the solvents and purification via silica gel chromatography (10-30% ethyl acetate/hexanes with 1% acetic acid) afforded the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.04-1.23 (m, 2 H), 1.41-1.57 (m, 2 H), 1.58-1.67 (m, 1 H), 1.69-1.77 (m, 1 H), 1.78-1.88 (m, 4 H), 2.12-2.20 (m, 2 H), 7.05-7.17 (m, 1 H), 7.26-7.41 (m, 2 H), 7.62-7.82 (m, 2 H), 12.00 (s, 1 H), 13.89-14.07 (m, 1 H); MS (ESI) m/z 354 [M+H]+.

Workup

  1. waitAfter 16 hours
  2. customthe reaction was quenched with 1 N HCl
  3. filtrationthe mixture filtered over a bed of celite
  4. customEvaporation of the solvents and purification via silica gel chromatography (10-30% ethyl acetate/hexanes with 1% acetic acid)

Sources & evidence

ORD record
ord-ea1306ee86c345b39dbbe4ffa21d6c67
Source dataset
uspto-grants-2012_06
Patent number
US08202878B2

Reaction notes

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