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Diisopropylethylamine → Methyl succinimidyl hexadecandioate

HRID 1434501
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HRID 1434501 반응식
[C:1]([O:20][CH3:21])(=[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][C:16]([O-:18])=[O:17].F[B-](F)(F)F.[C:27]1(=[O:41])[N:31](OC(N(C)C)=[N+](C)C)[C:30](=[O:40])[CH2:29][CH2:28]1.C(N(CC)C(C)C)(C)C>C1COCC1>[C:1]([O:20][CH3:21])(=[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][C:16]([O:18][N:31]1[C:27](=[O:41])[CH2:28][CH2:29][C:30]1=[O:40])=[O:17]
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참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 98575222-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborateHCID 85704850Hexadecanedioic acid, monomethyl ester

생성물 1

HCID 86607066Methyl succinimidyl hexadecandioate수율 96.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Mono-methyl hexadecandioate (275 mg, 0.91 mmol) was dissolved in THF (3 ml) and treated with succinimidyl tetramethyluroniumtetrafluoroborate (331 mg, 1.1 mmol) and N,N-diisopropylethylamine (188 μL, 1.1 mmol), and the mixture was stirred for 20 hours. The solvent was removed in vacuo, and the residue was dissolved in ethyl acetate and washed with 0.1 M HCl (twice) and water. The organic phase was dried over MgSO4, filtered and evaporated in vacuo to give 350 mg (96%) of methyl succinimidyl hexadecandioate.

후처리

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with 0.1 M HCl (twice) and water
  4. dry with materialThe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-8caaf65e21f3408297b994b4a8a3e387
출처 데이터셋
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07615532B2

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