Sodium Hydroxide → HCID 22618858, compound

HRID 970055Notes

Reaction equation

HRID 970055 reaction equation
C([NH:4][C:5]([CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[CH:20][CH:19]=1)(C(OCC)=O)[C:6]([O:8]CC)=[O:7])(=O)C.[OH-].[Na+]>>[NH2:4][CH:5]([CH2:16][CH2:17][C:18]1[CH:19]=[CH:20][C:21]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[CH:22][CH:23]=1)[C:6]([OH:8])=[O:7]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 98457531,3-Diethyl 2-(acetylamino)-2-(2-(4-octylphenyl)ethyl)propanedioate

Product 1

HCID 22618858HCID 22618858, compoundYield 99.8%

Conditions

Temperature
100 °C

Procedure

A mixture of 13.25 g (30.6 mmol) of diethyl 2-acetamido-2-(2-(4-octylphenyl)ethyl)propandioate (prepared according to the procedure described by Durand, et.al., Synthesis, 2000, 505-506, which is hereby incorporated by reference in its entirety) and 75 mL of concentrated HCL were stirred at 100° C. for 16 h. The mixture was cooled and 75 g of ice was added. The mixture was neutralized (pH=7) with 5 N NaOH. The precipitate was filtered, rinsed with water and dried to afford 8.9 g of the title compound: HPLC B: 2.68 min; ESI-MS 292 (M+H).

Workup

  1. customprepared
  2. custom, Synthesis, 2000, 505-506, which
  3. temperatureThe mixture was cooled
  4. filtrationThe precipitate was filtered
  5. washrinsed with water
  6. customdried

Sources & evidence

ORD record
ord-2579f87c7649436d9422eeecdd30ed4e
Source dataset
uspto-grants-2007_12
Patent number
US07309721B2

Reaction notes

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