Triethylamine → Di-tert-butyl 4-(2-bromoacetamido)-4-(3-(tert-butoxy)-3-oxopropyl)heptanedioate

HRID 2273338노트

반응식

HRID 2273338 반응식
[NH2:1][C:2]([CH2:21][CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])([CH2:12][CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:3][CH2:4][C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].[Br:30][CH2:31][C:32](Br)=[O:33].CCN(CC)CC>C(Cl)Cl>[Br:30][CH2:31][C:32]([NH:1][C:2]([CH2:12][CH2:13][C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])([CH2:3][CH2:4][C:5]([O:7][C:8]([CH3:11])([CH3:9])[CH3:10])=[O:6])[CH2:21][CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[O:33]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 61147Bromoacetyl bromideHCID 10927842Aminotriester

생성물 1

HCID 24728093Di-tert-butyl 4-(2-bromoacetamido)-4-(3-(tert-butoxy)-3-oxopropyl)heptanedioate수율 40.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of di-tert-butyl 4-amino-4-(3-(tert-butoxy)-3-oxopropyl)heptanedioate (5.00 g, 12.0 mmol) and 2-bromoacetyl bromide (1.46 mL, 3.40 g, 16.80 mmol) in DCM (60 mL) was added Et3N (2.5 mL) at room temperature. The reaction mixtures were stirred at room temperature for overnight. The reaction mixtures were diluted with DCM (300 mL), washed with 1N HCl solution, and dried over Na2SO4. Solvent was evaporated under reduce pressure to afford a residue, which was purified by biotage eluting with 10% EtOC in hexanes to 100% EtOAc to afford di-tert-butyl 4-(2-bromoacetamido)-4-(3-(tert-butoxy)-3-oxopropyl)heptanedioate (2.58 g, 40%). 1H NMR (400 MHz, CDCl3) 6.43 (s, 1H), 3.76 (s, 2H), 2.20 (t, J=8.0 Hz, 2H), 1.98 (t, J=8.0 Hz, 6H), 1.43 (s, 27H); MS (ESI), 558, 560 (M+Na)+.

후처리

  1. customThe reaction mixtures
  2. customThe reaction mixtures
  3. washwashed with 1N HCl solution
  4. dry with materialdried over Na2SO4
  5. customSolvent was evaporated
  6. customto afford a residue, which
  7. customwas purified by biotage
  8. washeluting with 10% EtOC in hexanes to 100% EtOAc

출처 및 근거

ORD 기록
ord-f3e291e2023a4840a9e291120f18d434
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09120837B2

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