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

HRID 2280241Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2280241
[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]

Komponenten

5

Edukt 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 10927842Aminotriester

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-65ab3c6af2a04f2e9ee8be0e5f6ae8a0
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09138495B2

Notizen zur Reaktion

Wird geladen…