Water → HCID 53699280, compound

HRID 355145Notes

Reaction equation

HRID 355145 reaction equation
[OH-].[Na+].O.[CH3:4][C@H:5]1[CH2:10][C@@H:9]([CH3:11])[CH2:8][N:7]([S:12]([C:15]2[CH:16]=[CH:17][CH:18]=[C:19]([C:24]=2[Cl:25])[C:20]([O:22]C)=[O:21])(=[O:14])=[O:13])[CH2:6]1>CO>[CH3:4][C@H:5]1[CH2:10][C@@H:9]([CH3:11])[CH2:8][N:7]([S:12]([C:15]2[CH:16]=[CH:17][CH:18]=[C:19]([C:24]=2[Cl:25])[C:20]([OH:22])=[O:21])(=[O:13])=[O:14])[CH2:6]1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 54351328HCID 54351328, compound

Product 1

HCID 53699280HCID 53699280, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

An aqueous solution of 4.2 g. (105 m moles) of sodium hydroxide in 130 ml. of water is added to 18 g. (52.5 m moles) of methyl 5-(cis-3,5-dimethylpiperidinosulfonyl)-6-chlorobenzoate in 130 ml. of methanol, and resulting reaction mixture allowed to stir at 40° C. for 1 hr. The solution is poured into ice water (1.5 l.) and extracted several times with benzene. The aqueous phase is separated, acidified with 12 N hydrochloric acid, and the precipitated product filtered and air dried, 17.3 g. Recrystallization from ethyl acetate-hexane gave the purified product, 16.4 g., m.p. 152.5°-153° C.

Workup

  1. customreaction mixture
  2. extractionextracted several times with benzene
  3. customThe aqueous phase is separated
  4. filtrationthe precipitated product filtered
  5. customair dried
  6. customRecrystallization from ethyl acetate-hexane
  7. customgave the purified product, 16.4 g

Sources & evidence

ORD record
ord-2b87d682e55c4455882caf8fb1a49542
Source dataset
uspto-grants-1983_03
Patent number
US04377521

Reaction notes

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