Sodium Hydroxide → N-[4-[14-(Trimethylsilyl)tetradecylamino]benzoyl)glycine

HRID 652032

Reaction equation

HRID 652032 reaction equation
[CH3:1][Si:2]([CH3:34])([CH3:33])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18]1[CH:32]=[CH:31][C:21]([C:22](=[O:30])[NH:23][CH2:24][C:25]([O:27]CC)=[O:26])=[CH:20][CH:19]=1.[OH-].[Na+]>C(O)C>[CH3:34][Si:2]([CH3:1])([CH3:33])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18]1[CH:19]=[CH:20][C:21]([C:22]([NH:23][CH2:24][C:25]([OH:27])=[O:26])=[O:30])=[CH:31][CH:32]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 20198242Ethyl 4-[14-(trimethylsilyl)tetradecylamino]hippurate

Product 1

HCID 20198286N-[4-[14-(Trimethylsilyl)tetradecylamino]benzoyl)glycine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 12.5 g. of ethyl 4-[14-(trimethylsilyl)tetradecylamino]hippurate, 55 ml. of 1N sodium hydroxide solutions and 50 ml. of ethanol is stirred at ambient temperature for 2 hours and then partially evaporated. The aqueous solution is washed with diethyl ether, acidified with 6N hydrochloric acid, and filtered. The solid is dried in vacuo and recrystallized to yield the product as a white solid.

Workup

  1. additionA mixture of 12.5 g
  2. custompartially evaporated
  3. washThe aqueous solution is washed with diethyl ether
  4. filtrationfiltered
  5. customThe solid is dried in vacuo
  6. customrecrystallized

Sources & evidence

ORD record
ord-51d702da3ab148408fdf35a26672fdea
Source dataset
uspto-grants-1987_06
Patent number
US04670421

Linked notes

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