Phosphoric Acid → 290334-34-8

HRID 1395905Notes

Reaction equation

HRID 1395905 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].[P:21](=[O:25])([OH:24])([OH:23])[OH:22]>C(OCC)(=O)C>[P:21](=[O:22])([OH:25])([OH:24])[OH: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 1004Phosphoric AcidHCID 3025823Dodecyl N,N-dimethylalaninate2×

Product 1

HCID 76283008290334-34-8Yield 93%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A stirred solution of DDAIP base 4 (100 g, 350 mmol) in ethyl acetate (500 mL) was cooled to 0° C. and then phosphoric acid 12 (34.38 g, 350 mmol) was added in one lot. After addition, the temperature of the reaction mixture was slowly raised to RT and stirred at RT for 12 h; the reaction mixture was monitored by TLC. The reaction mixture was concentrated under vacuum. The obtained sticky solid was taken in n-hexane (200 mL) and stirred at RT for 2 h to afford dodecyl 2-(dimethylamino)propanoate phosphorate salt (13, Nex-15) (125 g, 93%) as a sticky solid. 1H-NMR (400 MHz, CDCl3): δ 0.85 (t, 3H), 1.2-1.4 (m, 18H), 1.55 (d, 3H), 1.7 (q, 2H), 2.85 (s, 6H), 4.1 (q, 1H), 4.2 (t, 2H); LCMS: 286 (M++1); HPLC: 95.8%.

Workup

  1. additionAfter addition
  2. concentrationThe reaction mixture was concentrated under vacuum
  3. stirringstirred at RT for 2 h

Sources & evidence

ORD record
ord-d874ed4e53c34f158a686179a0988827
Source dataset
uspto-grants-2014_12
Patent number
US08900625B2

Reaction notes

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