Benzenesulfonic Acid → HCID 76280825, compound

HRID 1395906Notes

Reaction equation

HRID 1395906 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].[C:21]1([S:27]([OH:30])(=[O:29])=[O:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(OCC)(=O)C>[C:21]1([S:27]([OH:30])(=[O:29])=[O:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[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 7371Benzenesulfonic AcidHCID 3025823Dodecyl N,N-dimethylalaninate2×

Product 1

HCID 76280825HCID 76280825, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A stirred solution of DDAIP base 4 (75 g, 263 mmol) in ethyl acetate (500 mL) was cooled to 0° C., then benzene sulfonic acid 14 (41.55 g, 263 mmol) was added in one lot. After addition, the temperature of the reaction mixture was slowly raised to RT and stirred at RT for 24 h; the reaction mixture was monitored by TLC. The reaction mixture was concentrated under vacuum. The residue washed with hexane (2×30 mL); after workup a sticky solid was observed. The obtained sticky solid was kept in deep freezer for 12 h to afford dodecyl 2-(dimethylamino)propanoate benzene sulfonate salt (15, Nex-16) (116 g, yield: 99.5%) as a solid, mp: 55-62° C. 1H-NMR (400 MHz, CDCl3): δ 0.9 (t, 3H), 1.3 (m, 18H), 1.65 (d, 3H), 1.65 (q, 2H), 3 (s, 6H), 4.2 (q, 1H), 4.2 (t, 2H), 7.4 (m, 3H), 7.9 (d, 2H); LCMS: 286 (M++1); HPLC: 80.48%.

Workup

  1. additionAfter addition
  2. concentrationThe reaction mixture was concentrated under vacuum
  3. washThe residue washed with hexane (2×30 mL)
  4. waitThe obtained sticky solid was kept in deep freezer for 12 h

Sources & evidence

ORD record
ord-4fb5b8046f4b428b87b352d894426fd4
Source dataset
uspto-grants-2014_12
Patent number
US08900625B2

Reaction notes

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