Lithium Hydroxide → HCID 67052321, compound

HRID 1918224Notes

Reaction equation

HRID 1918224 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:29])=[C:6]([CH:28]=1)[C:7]([NH:9][C:10]1[C:11]([C:24]([O:26]C)=[O:25])=[C:12]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[C:17]([F:22])[C:16]=2[F:23])[S:13][CH:14]=1)=[O:8].[OH-].[Li+]>O1CCCC1.CO.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:29])=[C:6]([CH:28]=1)[C:7]([NH:9][C:10]1[C:11]([C:24]([OH:26])=[O:25])=[C:12]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[C:17]([F:22])[C:16]=2[F:23])[S:13][CH:14]=1)=[O:8]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67052221HCID 67052221, compound

Product 1

HCID 67052321HCID 67052321, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Ester 395 (74.1 mg, 169 μmol) and lithium hydroxide (24.3 mg, 1.0 mmol) in tetrahydrofuran:methanol:water (3:2:1, 0.9 mL) was stirred at 60° C. for 2 h. The mixture was cooled, quenched with 2 M HCl (1.0 mL) and diluted with water (3 mL). The precipitate that formed was filtered and washed with methanol:water (1:2, 1 mL) and dichloromethane (1 mL) to provide 396 (55 mg, 77%) as a solid: LRESIMS m/z 424.1 [M+H]+, calcd. for C19H13Cl1F2N1O4S1 424.0.

Workup

  1. temperatureThe mixture was cooled
  2. customquenched with 2 M HCl (1.0 mL)
  3. additiondiluted with water (3 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-4d709683bd66468e95992cd16ca8eeff
Source dataset
uspto-grants-2013_12
Patent number
US08618307B2

Reaction notes

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