1,2-Dimethoxyethane → 12-(Hexadecanoylamino)dodecanoic acid

HRID 728236Notes

Reaction equation

HRID 728236 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14].[O:16]1[CH2:21][CH2:20]OCC1.[CH2:22]([CH2:25]OC)OC>>[O:16]=[C:21]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])[CH2:20][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:22][CH3:25]

Participants

4

Reactant 3

HCID 80711,2-DimethoxyethaneHCID 312751,4-DioxaneHCID 6966112-Aminododecanoic Acid

Product 1

HCID 1982410812-(Hexadecanoylamino)dodecanoic acidYield 72%

Procedure

A sample of 5.13 g (20.0 mmol) hexadecanoic acid, 2.30 g (20.0 mmol) N-hydroxysuccinimide and 4.53 g (22.0 mmol) dicyclohexylcarbodiimide (DOC) was dissolved in 20 ml dry tetrahydrofurane or methylenechloride. The temperature of the reaction mixture was kept at 20° C. and the mixture stirred overnight under an atmosphere of nitrogen. The precipitate was removed by filtration and the filtrate concentrated by rotoevaporation to dryness to yield 6.0 g (85%) of the succinimidylester. 180 mg (0.509 mmol) of this active ester and 110 mg (0.510 mmol) 12-aminododecanoic acid were suspended in 3 ml dry dimethoxyethane or dioxane and stirred at 50°-60° C. for ca. 4 h. The reaction mixture was filtered hot and diluted with ice water. The precipitate was removed by filtration and purified by crystallization from methanol to yield 165 mg (72%) of the product as colourless cystals, m.p. 119°-121° C.

Workup

  1. filtrationThe reaction mixture was filtered hot
  2. additiondiluted with ice water
  3. customThe precipitate was removed by filtration
  4. custompurified by crystallization from methanol

Sources & evidence

ORD record
ord-ae25a58b64f34ad19c799c7c1199bb3b
Source dataset
uspto-grants-1991_09
Patent number
US05047535

Reaction notes

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