Lithium Hydroxide → HCID 67052205, compound

HRID 1918222Notes

Reaction equation

HRID 1918222 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([OH:28])=[C:6]([CH:27]=1)[C:7]([NH:9][C:10]1[C:11]([C:23]([O:25]C)=[O:24])=[C:12]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][C:16]=2[F:22])[S:13][CH:14]=1)=[O:8].[OH-].[Li+]>O1CCCC1.CO.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([OH:28])=[C:6]([CH:27]=1)[C:7]([NH:9][C:10]1[C:11]([C:23]([OH:25])=[O:24])=[C:12]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][C:16]=2[F:22])[S:13][CH:14]=1)=[O:8]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67052260HCID 67052260, compound

Product 1

HCID 67052205HCID 67052205, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Ester 385 (61 mg, 151 μmol) and lithium hydroxide (21.7 mg, 907 μmol) in tetrahydrofuran:methanol:water (3:2:1, 0.8 mL) was stirred at 60° C. for 2 h. The mixture was cooled, quenched with 2 M HCl (0.7 mL) and diluted with water (2 mL). The precipitate that formed was filtered and washed with methanol:water (1:2, 1 mL) and dichloromethane (1 mL) to provide 386 (38.2 mg, 65%) as a solid: LRESIMS m/z 390.1 [M+H]+, calcd. for C19H14F2N1O4S1 390.1.

Workup

  1. temperatureThe mixture was cooled
  2. customquenched with 2 M HCl (0.7 mL)
  3. additiondiluted with water (2 mL)
  4. customThe precipitate that formed
  5. filtrationwas filtered
  6. washwashed with methanol:water (1:2, 1 mL) and dichloromethane (1 mL)

Sources & evidence

ORD record
ord-1e87ce08a56a487bba11552f3811911a
Source dataset
uspto-grants-2013_12
Patent number
US08618307B2

Reaction notes

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