Water → 4-(2-(12-(Isopropylthio)dodecanoylamino)phenoxy)-butyric acid

HRID 1003236Notes

Reaction equation

HRID 1003236 reaction equation
[CH:1]([S:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([NH:18][C:19]1[CH:33]=[CH:32][CH:31]=[CH:30][C:20]=1[O:21][CH2:22][CH2:23][CH2:24][C:25]([O:27]CC)=[O:26])=[O:17])([CH3:3])[CH3:2].[OH-].[Na+].O>CO>[CH:1]([S:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([NH:18][C:19]1[CH:33]=[CH:32][CH:31]=[CH:30][C:20]=1[O:21][CH2:22][CH2:23][CH2:24][C:25]([OH:27])=[O:26])=[O:17])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 18796054Ethyl 4-(2-(12-(Isopropylthio)dodecanoylamino)-phenoxy)-butyrate

Product 1

HCID 187956624-(2-(12-(Isopropylthio)dodecanoylamino)phenoxy)-butyric acidYield 17.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A stirred solution of ester (7) (0.124 g, 0.258 mM) in methanol (10 mL) was treated at room temperature under a nitrogen atmosphere with 2.5N sodium hydroxide solution (0.6 mL). Methanol (2×2 mL) was used to clear the mixture, and the reaction allowed to continue until TLC analysis showed no ester remained. The filtered mixture was concentrated in vacuo and the residue obtained stirred with water (30 mL). After aging, the mixture was filtered (The cake is the sodium salt of the product (100 mg), and the stirred filtrate acidified with dilute hydrochloric acid, aged, filtered, washed with water and dried to give product 8 (0.02 g) as a white solid. M.P. 82-84° C., with softening from 66° C.

Workup

  1. concentrationThe filtered mixture was concentrated in vacuo
  2. customthe residue obtained
  3. filtrationthe mixture was filtered (The cake
  4. filtrationfiltered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-ff153ea28589468a897d489d92249c25
Source dataset
uspto-grants-2000_04
Patent number
US06046183

Reaction notes

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