Acetyl chloride → 4-Acetylamino-4-(2-tert-butoxycarbonyl-ethyl)-heptanedioic acid di-tert-butyl ester

HRID 2280241노트

반응식

HRID 2280241 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].C(N(CC)CC)C.[C:37](Cl)(=[O:39])[CH3:38]>C(Cl)Cl>[C:26]([O:25][C:23](=[O:24])[CH2:22][CH2:21][C:2]([NH:1][C:37](=[O:39])[CH3:38])([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])([CH3:29])([CH3:28])[CH3:27]

참가 물질

5

반응물 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 10927842Aminotriester

생성물 1

HCID 867110904-Acetylamino-4-(2-tert-butoxycarbonyl-ethyl)-heptanedioic acid di-tert-butyl ester수율 72%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

To 5 ml CH2Cl2 was added 1 g of triester 62 (2.4 mmol, 1 equiv) and 0.3 g triethylamine (2.9 mmol, 1.2 equiv.) The solution was cooled to 0° C. with an ice bath and 0.23 g acetyl chloride (2.9 mmol, 1.2 equiv) was added dropwise. The solution was stirred for a further 4 hours and allowed to warm slowly to room temperature. The solution was poured into a separating funnel and washed with 2×15 ml HCl (5% aqueous) and 1×15 ml concentrated NaCl. The solution was dried over Na2SO4 and the solvent was removed in vacuo. The residue was dissolved in minimal EtOAc and loaded onto a silica column, where it was purified by column chromatography with EtOAc and hexane (1:1) to give 0.79 g of a white solid in 72% yield.

후처리

  1. temperatureto warm slowly to room temperature
  2. additionThe solution was poured into a separating funnel
  3. washwashed with 2×15 ml HCl (5% aqueous) and 1×15 ml concentrated NaCl
  4. dry with materialThe solution was dried over Na2SO4
  5. customthe solvent was removed in vacuo
  6. dissolutionThe residue was dissolved in minimal EtOAc
  7. customwas purified by column chromatography with EtOAc and hexane (1:1)

출처 및 근거

ORD 기록
ord-65ab3c6af2a04f2e9ee8be0e5f6ae8a0
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09138495B2

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