Methanesulfonic Acid → HCID 76280827, compound

HRID 1395908Notes

Reaction equation

HRID 1395908 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].[CH3:21][S:22]([OH:25])(=[O:24])=[O:23]>C(OCC)(=O)C>[CH3:21][S:22]([OH:25])(=[O:24])=[O:23].[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 6395Methanesulfonic AcidHCID 3025823Dodecyl N,N-dimethylalaninate2×

Product 1

HCID 76280827HCID 76280827, compoundYield 97.34%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A stirred solution of DDAIP base 4 (85 g, 298 mmol) in ethyl acetate (500 mL) was cooled to 0° C., then methane sulfonic acid 18 (28.6 g, 298 mmol) was added in one lot. After addition, the temperature of the reaction mixture was slowly raised to RT and stirred at RT for 48 h; the reaction mixture was monitored by TLC. The reaction mixture was concentrated under vacuum. The obtained residue was taken in n-hexane (30 mL) and stirred at RT for ½ h (No solid). The reaction mixture was concentrated under vacuum and flushed with hexane (3×30 mL) to afford dodecyl 2-(dimethylamino)propanoate methane sulfonate salt (19, Nex-22) (110 g, yield: 97.34%) as a solid, mp: 66-72° C. 1H-NMR (400 MHz, CDCl3): δ 0.9 (t, 3H), 1.35 (m, 18H), 1.65 (q, 2H), 1.7 (d, 3H), 2.8 (s, 3H), 3 (s, 6H), 4.15 (q, 1H), 4.2 (t, 2H); LCMS: 286 (M+); HPLC: 100%.

Workup

  1. additionAfter addition
  2. concentrationThe reaction mixture was concentrated under vacuum
  3. stirringstirred at RT for ½ h (No solid)
  4. concentrationThe reaction mixture was concentrated under vacuum
  5. customflushed with hexane (3×30 mL)

Sources & evidence

ORD record
ord-2f434a1ceff344cbaa875440e124fd8a
Source dataset
uspto-grants-2014_12
Patent number
US08900625B2

Reaction notes

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