Isethionic Acid → HCID 76280829, compound

HRID 1395911Notes

Reaction equation

HRID 1395911 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]([CH:16]([N:18]([CH3:20])[CH3:19])[CH3:17])=[O:15].[OH:21][CH2:22][CH2:23][S:24]([OH:27])(=[O:26])=[O:25]>C(OCC)(=O)C>[OH:21][CH2:22][CH2:23][S:24]([OH:27])(=[O:26])=[O:25].[CH3:19][N:18]([CH3:20])[CH:16]([CH3:17])[C:14]([O:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:15]

Participants

4

Reactant 2

HCID 7866Isethionic AcidHCID 3025823Dodecyl N,N-dimethylalaninate2×

Product 1

HCID 76280829HCID 76280829, compoundYield 96.15%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of DDAIP base 4 (85 g, 298 mmol) in ethyl acetate (500 mL) cooled to 0° C. was added 2-hydroxyethanesulfonic acid 24 (80% pure only) (45 g, 357 mmol) in one lot. After addition, the temperature of the reaction mixture was slowly raised to room temperature and stirred at RT for 12 h; the reaction mixture was monitored by TLC. The reaction mixture was concentrated under vacuum. The obtained residue was taken in n-hexane (20 mL) and stirred at RT for ½ h (No solid). The obtained sticky solid was kept in deep freezer for 48 h to afford dodecyl 2-(dimethylamino)propanoate 2-hydroxyethanesulfonate salt (25, Nex-46) (125 g, yield: 96.15%) as a waxy hygroscopic solid, Mp: 58-63° C. 1H-NMR (400 MHz, CDCl3): δ 0.8 (t, 31H), 1.2-1.3 (m, 181H), 1.6 (d, 3H), 2.9 (s, 6H), 3.05 (t, 2H), 3.9 (t, 2H), 4.1 (q, 2H), 4.2 (t, 2H); LCMS: 286 (M++1); HPLC: 100%.

Workup

  1. additionAfter addition
  2. concentrationThe reaction mixture was concentrated under vacuum
  3. stirringstirred at RT for ½ h (No solid)
  4. waitThe obtained sticky solid was kept in deep freezer for 48 h

Sources & evidence

ORD record
ord-9635d8ed5fb84f1a887f3530f42df960
Source dataset
uspto-grants-2014_12
Patent number
US08900625B2

Reaction notes

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