1,5-Naphthalenedisulfonic acid → HCID 86722540, compound

HRID 1395910Notes

Reaction equation

HRID 1395910 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:35]([OH:38])(=[O:37])=[O:36])[C:30]2[CH:29]=[CH:28][CH:27]=[C:26]([S:31]([OH:34])(=[O:33])=[O:32])[C:25]=2[CH:24]=[CH:23][CH:22]=1>CO>[C:21]1([S:35]([OH:38])(=[O:37])=[O:36])[C:30]2[CH:29]=[CH:28][CH:27]=[C:26]([S:31]([OH:34])(=[O:33])=[O:32])[C:25]=2[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 66661,5-Naphthalenedisulfonic acidHCID 3025823Dodecyl N,N-dimethylalaninate2×

Product 1

HCID 86722540HCID 86722540, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A stirred solution of DDAIP base 4 (80 g, 280 mmol) in methanol (500 mL) was cooled to 0° C., then 1,5-napthalene disulfonic acid 22 (50.5 g, 140 mmol) was added in one lot. After addition the temperature of the reaction mixture was slowly raised to RT and stirred at RT for 72 h; the reaction mixture was monitored by TLC. The reaction mixture was concentrated under vacuum and flushed with ethyl acetate (2×30 mL). The obtained residue was taken in n-hexane (200 mL) and stirred at RT for ½ h (sticky solid). The reaction mixture was concentrated under vacuum and flushed with hexane (3×100 mL) to afford dodecyl 2-(dimethylamino)propanoate 1,5-napthalene disulfonate salt (23, Nex-32) (120 g, 92.3%) as a white solid. Mp: 135-140° C. 1H-NMR (400 MHz, CDCl3): δ 0.9 (t, 3H), 1.2-1.3 (m, 18H), 1.6 (d, 3H), 1.65 (q, 2H), 2.9 (s, 6H), 4.15 (t, 2H), 4.2 (q, 1H), 7.55 (t, 2H), 8.22 (d, 2H), 9.1 (d, 2H); LCMS: 286 (M++1); HPLC: 80.48%.

Workup

  1. additionAfter addition the temperature of the reaction mixture
  2. concentrationThe reaction mixture was concentrated under vacuum
  3. customflushed with ethyl acetate (2×30 mL)
  4. stirringstirred at RT for ½ h (sticky solid)
  5. concentrationThe reaction mixture was concentrated under vacuum
  6. customflushed with hexane (3×100 mL)

Sources & evidence

ORD record
ord-4c1654e980a9489dae21b317a1123de2
Source dataset
uspto-grants-2014_12
Patent number
US08900625B2

Reaction notes

Loading…