6-Methacrylamidohexanoic acid → HCID 58173699, 화합물

HRID 2280187노트

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HRID 2280187 반응식
[C:1]([NH:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=O)(=[O:5])[C:2]([CH3:4])=[CH2:3].Br.[C:16]([O:20][C:21]([CH2:23][N:24]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31][N:30]([CH2:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:29][CH2:28][N:27]([CH2:44][C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[CH2:26][CH2:25]1)=[O:22])([CH3:19])([CH3:18])[CH3:17].Cl.C(N=C=NCCCN(C)C)C>ClCCl>[C:16]([O:20][C:21](=[O:22])[CH2:23][N:24]1[CH2:35][CH2:34][N:33]([C:12](=[O:14])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][NH:6][C:1](=[O:5])[C:2]([CH3:4])=[CH2:3])[CH2:32][CH2:31][N:30]([CH2:36][C:37]([O:39][C:40]([CH3:41])([CH3:42])[CH3:43])=[O:38])[CH2:29][CH2:28][N:27]([CH2:44][C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[CH2:26][CH2:25]1)([CH3:17])([CH3:18])[CH3:19]

참가 물질

5

반응물 3

HCID 1009776-Methacrylamidohexanoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride2회HCID 21832608Tri-tert-butyl 2,2',2''-(1,4,7,10-tetraazacyclododecane-1,4,7-triyl)triacetate--hydrogen bromide (1/1)

생성물 1

HCID 58173699HCID 58173699, 화합물수율 113.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
-5 °C

실험 절차

A suspension of 6-(methacryloylamino)caproic acid (2.80 g, 14.0 mmol), 1,4,7-tris(tert-butoxycarbonylmethyl)-1,4,7,10-tetraazacyclododecane hydrobromide (7.75 g, 13.0 mmol), N,N-dimethylaminopyridine (1.83 g, 15.0 mmol) and 5 mg BHT in 60 ml dichloromethane was cooled to −5° C. and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (2.88 g, 15.0 mmol) was added portionwise under stirring. To complete the reaction, the mixture was stirred for 2 h at −5° C. and over night at room temperature. 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.00 g, 6.44 mmol) and N,N-dimethylaminopyridine (0.6 g, 4.9 mmol) each time were then added 3 more times at intervals of 2 h and finally left to be stirred for 6 h. The solution was washed 3 times with in each case 50 ml saturated aqueous NaCl solution, dried over anhydrous Na2SO4, filtered, concentrated on the rotary evaporator after the addition of 5 mg BHT and dried under fine vacuum. 10.3 g of a yellowish oil was obtained which was purified twice by chromatography (silica gel 60, 0.015-0.040 mm, acetone). The acetone was again distilled off on the rotary evaporator after the addition of 5 mg BHT and the product dried in fine vacuum. 6.13 g (8.8 mmol, 68% yield) of a yellow, highly viscous oil was obtained (HPLC purity: 95%).

후처리

  1. customthe reaction
  2. stirringthe mixture was stirred for 2 h at −5° C. and over night at room temperature
  3. waitfinally left
  4. stirringto be stirred for 6 h
  5. washThe solution was washed 3 times with in each case 50 ml saturated aqueous NaCl solution
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated on the rotary evaporator
  9. additionafter the addition of 5 mg BHT
  10. customdried under fine vacuum

출처 및 근거

ORD 기록
ord-22b3e519ba3d4885a1328883ebb56bcc
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09138382B2

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