Lithium Hydroxide → HCID 51033466, compound

HRID 1918221Notes

Reaction equation

HRID 1918221 reaction equation
[F:1][C:2]1[C:7]([F:8])=[C:6]([CH3:9])[CH:5]=[CH:4][C:3]=1[C:10]1[S:11][CH:12]=[C:13]([NH:19][C:20]([C:22]2[CH:31]=[C:25]3[C:26]([F:30])=[CH:27][CH:28]=[CH:29][N:24]3[N:23]=2)=[O:21])[C:14]=1[C:15]([O:17]C)=[O:16].[OH-].[Li+]>O1CCCC1.CO.O>[F:1][C:2]1[C:7]([F:8])=[C:6]([CH3:9])[CH:5]=[CH:4][C:3]=1[C:10]1[S:11][CH:12]=[C:13]([NH:19][C:20]([C:22]2[CH:31]=[C:25]3[C:26]([F:30])=[CH:27][CH:28]=[CH:29][N:24]3[N:23]=2)=[O:21])[C:14]=1[C:15]([OH:17])=[O:16]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67052371HCID 67052371, compound

Product 1

HCID 51033466HCID 51033466, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Ester 379 (1.45 g, 3.3 mmol) and lithium hydroxide (467 mg, 19.5 mmol) in tetrahydrofuran:methanol:water (3:2:1, 16 mL) was stirred at 50° C. for 1 h. The mixture was cooled in an ice bath and quenched with 2 M HCl (16 mL). The precipitate that formed was filtered off to provide 368 (1.40 g, 100%) as a solid: LRESIMS m/z 432.0 [M+H]+, calcd. for C20H13F3N3O3S1 432.1.

Workup

  1. temperatureThe mixture was cooled in an ice bath
  2. customquenched with 2 M HCl (16 mL)
  3. customThe precipitate that formed
  4. filtrationwas filtered off

Sources & evidence

ORD record
ord-7dee355a81e54798a808b045e2f3b25f
Source dataset
uspto-grants-2013_12
Patent number
US08618307B2

Reaction notes

Loading…