Citric Acid → HCID 76280824, compound

HRID 1395904Notes

Reaction equation

HRID 1395904 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]([OH:33])(=[O:32])[CH2:22][C:23]([CH2:28][C:29]([OH:31])=[O:30])([C:25]([OH:27])=[O:26])[OH:24]>CO>[C:21]([OH:33])(=[O:32])[CH2:22][C:23]([CH2:28][C:29]([OH:31])=[O:30])([C:25]([OH:27])=[O:26])[OH:24].[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 311Citric AcidHCID 3025823Dodecyl N,N-dimethylalaninate2×

Product 1

HCID 76280824HCID 76280824, compoundYield 95.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A stirred solution of DDAIP base 4 (75 g, 263 mmol) in methanol (600 mL) was cooled to 0° C. then citric acid 8 (50.4 g, 0.263) 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 solvent was concentrated under vacuum. The residue was diluted with n-hexane (100 mL) which was not miscible with the product. Some seeding material was prepared (scratching the crude in a glass vial), and seeded to the crude to afford dodecyl 2-(dimethylamino)propanoate citrate salt (11, Nex-07) (120 g, yield: 95.6%) as a white solid, mp: 62-67° C. 1H-NMR (400 MHz, CDCl3): δ 0.85 (t, 3H), 1.3 (m, 18H), 1.5 (d, 3H), 1.7 (q, 2H), 2.7 (m, 2H), 2.9 (s, 6H), 4.1 (q, 1H), 4.2 (t, 2H); LCMS: 286 (M++1); HPLC: 88%.

Workup

  1. additionAfter addition
  2. concentrationThe solvent was concentrated under vacuum
  3. additionThe residue was diluted with n-hexane (100 mL) which
  4. customSome seeding material was prepared (

Sources & evidence

ORD record
ord-e6a166b652f74ebb837b0a343b7173e1
Source dataset
uspto-grants-2014_12
Patent number
US08900625B2

Reaction notes

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