Stearoyl chloride → Octadecanoic acid 2-(2-aminoethoxy)ethyl ester hydrochloride

HRID 480540

반응식

HRID 480540 반응식
[C:1]([Cl:20])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].Cl.[NH2:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][OH:28]>CN(C=O)C.CC(C)=O>[ClH:20].[NH2:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][O:28][C:1](=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

참가 물질

5

반응물 2

HCID 8212Stearoyl chlorideHCID 18764647HO-Peg-amine hcl

생성물 1

HCID 85772808Octadecanoic acid 2-(2-aminoethoxy)ethyl ester hydrochloride수율 40%

시약·촉매·용매 2

HCID 180Acetone용매HCID 6228Dimethylformamide용매

실험 절차

Stearoyl chloride (6.4 g; 21 mmol) (commercial product) was added dropwise in 5 min to a solution of 2-(2-aminoethoxy)ethanol hydrochloride (2.9 g; 20 mmol) in DMF (50 mL) at room temperature to afford a suspension. After 16 h, the suspension was diluted with acetone and the precipitated solid filtered and washed with acetone. The crude was crystallized from EtOAc; the solid was filtered, washed with EtOAc and dried under reduced pressure to give the desired compound (3.3 g; 8 mmol). Yield 40%. Acidic titer (0.1 N NaCH): 93%. K.F.: 1.06%. The 1H-NMR, 13C-NMR, MS and IR spectra were consistent with the structure.

후처리

  1. customto afford a suspension
  2. filtrationthe precipitated solid filtered
  3. washwashed with acetone
  4. customThe crude was crystallized from EtOAc
  5. filtrationthe solid was filtered
  6. washwashed with EtOAc
  7. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-dd7104a734f3465185cca07e169ffb5a
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06652834B2

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