Ethanesulfonic acid → HCID 76280828, compound

HRID 1395909Notes

Reaction equation

HRID 1395909 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].[CH2:21]([S:23]([OH:26])(=[O:25])=[O:24])[CH3:22]>C(OCC)(=O)C>[CH2:21]([S:23]([OH:26])(=[O:25])=[O:24])[CH3:22].[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 11668Ethanesulfonic acidHCID 3025823Dodecyl N,N-dimethylalaninate2×

Product 1

HCID 76280828HCID 76280828, compoundYield 98.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A stirred solution of DDAIP base 4 (85 g, 298 mmol) in ethyl acetate (600 mL) was cooled to 0° C., then ethane sulfonic acid 20 (32.79 g, 298 mmol) was added in one lot. After addition, the temperature of the reaction mixture was slowly raised to RT, stirred at RT for 12 h and the reaction mixture was monitored by TLC. The reaction mixture was concentrated under vacuum and flushed with hexane. The obtained residue was taken in n-hexane (200 mL) and stirred at RT for 2 h (No solid). The obtained sticky solid kept in deep freezer for 12 h to afford dodecyl 2-(dimethylamino)propanoate ethane sulfonate salt (21, Nex-30) (116 g, yield: 98.4%) as a hygroscopic solid, Mp: 45-50° C. 1H-NMR (400 MHz, CDCl3): δ 0.9 (t, 31H), 1.3 (m, 18H), 1.35 (t, 3H), 1.7 (d, 31H), 1.8 (q, 21H), 2.9 (q, 2H), 3 (m, 6H), 4.2 (m, 2H), 4.2 (m, 1H); LCMS: 286 (M++1); HPLC: 99.47%.

Workup

  1. additionAfter addition
  2. concentrationThe reaction mixture was concentrated under vacuum
  3. customflushed with hexane
  4. stirringstirred at RT for 2 h (No solid)
  5. waitThe obtained sticky solid kept in deep freezer for 12 h

Sources & evidence

ORD record
ord-f3508b9f0ec547798ef5fc6ff9d3ae51
Source dataset
uspto-grants-2014_12
Patent number
US08900625B2

Reaction notes

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