Water → HCID 87416741, compound

HRID 600945Notes

Reaction equation

HRID 600945 reaction equation
C[O:2][C:3](=[O:23])/[C:4](/[C:12]1[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[C:14]([Cl:22])[CH:13]=1)=[N:5]/[O:6][CH:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1.[OH-].[Li+].O>CO.C(Cl)(Cl)Cl>[Cl:22][C:14]1[CH:13]=[C:12](/[C:4](=[N:5]\[O:6][CH:7]2[CH2:11][CH2:10][CH2:9][CH2:8]2)/[C:3]([OH:23])=[O:2])[CH:17]=[CH:16][C:15]=1[S:18]([CH3:21])(=[O:20])=[O:19]

Participants

6

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 87416800methyl (2E)-2-(3-chloro-4-methylsulfonylphenyl)-2-cyclopentyloxyiminoacetate

Product 1

HCID 87416741HCID 87416741, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

(E)-(3-Chloro-4-methanesulfonyl-phenyl)-cyclopentyloxyimino-acetic acid methyl ester (144 mg, 0.40 mmol) was dissolved in methanol (4 mL) and cooled in an ice bath. A 2.0 N solution of lithium hydroxide in water (0.60 mL, 1.2 mmol) was added dropwise. After stirring 1 h, the reaction mixture was diluted with chloroform (50 mL) and washed with 0.1 M aqueous potassium bisulfate (25 mL). The aqueous phase was extracted with chloroform (30 mL) and the combined organic phases were dried over magnesium sulfate and evaporated in vacuo to afford (E)-(3-chloro-4-methanesulfonyl-phenyl)-cyclopentyloxyimino-acetic acid which was used in the next step without further purification: H1-NMR (400 MHz, CDCl3) δ=1.65 (4H, m), 1.88 (4H, m), 3.31 (3H, s), 4.97 (1H, m), 7.58 (1H, dd, J=8.2 Hz, J=1.1 Hz), 7.67 (1H, d, J=1.1 Hz), 8.19 (1H, d, J=8.2 Hz).

Workup

  1. temperaturecooled in an ice bath
  2. washwashed with 0.1 M aqueous potassium bisulfate (25 mL)
  3. extractionThe aqueous phase was extracted with chloroform (30 mL)
  4. dry with materialthe combined organic phases were dried over magnesium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-93ac6b35d6474007821a7cc503a93a59
Source dataset
uspto-grants-2011_03
Patent number
US07902248B2

Reaction notes

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