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Triethylamine → HCID 90060133, Verbindung

HRID 1779201
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1779201
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C@H:13]([NH:18][C:19]([C@@H:21](/[CH:34]=[CH:35]/[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][C:42](=[O:50])[CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])[C@@:22]([OH:33])(CCO)[C:23]([O:25]C(C)(C)C)=[O:24])=[O:20])[C:14]([O:16][CH3:17])=[O:15])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4].F[C:52](F)(F)[C:53]([O:55][C:56](=[O:61])[C:57](F)(F)F)=O.C(N(CC)CC)C>CN(C1C=CN=CC=1)C.ClCCl>[C:56]([O:55][CH2:53][CH2:52][C@:22]([OH:33])([C@@H:21]([C:19](=[O:20])[NH:18][C@H:13]([C:14]([O:16][CH3:17])=[O:15])[CH2:12][C:9]1[CH:8]=[CH:7][C:6]([O:5][CH2:1][C:2]#[C:3][CH3:4])=[CH:11][CH:10]=1)/[CH:34]=[CH:35]/[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][C:42](=[O:50])[CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])[C:23]([OH:25])=[O:24])(=[O:61])[CH3:57]
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Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydride2×HCID 90060183HCID 90060183, Verbindung

Produkt 1

HCID 90060133HCID 90060133, VerbindungAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysator
HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a mixture of No. 5217614, tert-butyl (E)-(2S,3S)-3-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-2-hydroxy-2-(2-hydroxy-ethyl)-12-oxo-nonadec-4-enoate (150 mg, 0.214 mmol) and dichloromethane (15 mL) were added trifluoroacetic acid anhydride (TFAA, 36 μL, 0.258 mmol), triethylamine (89 μL, 0.642 mmol), and DMAP (1.3 mg, 0.0107 mmol), and the mixture was stirred at room temperature. After being stirred for 3 hours, trifluoroacetic acid anhydride (72 μL, 0.516 mmol) was added again. After confirming the consumption of No. 5217614 tert-butyl (E)-(2S,3S)-3-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-2-hydroxy-2-(2-hydroxy-ethyl)-12-oxo-nonadec-4-enoate by LCMS, formic acid (5 mL) was added and the mixture was stirred overnight. The solvent was distilled off under reduced pressure. THF (5 mL) and a saturated aqueous solution (0.5 mL) of NaHCO3 were then added and the mixture was stirred at room temperature for 10 minutes. The solvent was distilled off under reduced pressure. The residue was then purified by preparative HPLC. The purified fraction was freeze-dried to obtain the title compound (67 mg, 48% yield, yellow oil).

Aufarbeitung

  1. additionTo a mixture of No
  2. stirringAfter being stirred for 3 hours
  3. customthe consumption of No
  4. addition5217614 tert-butyl (E)-(2S,3S)-3-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-2-hydroxy-2-(2-hydroxy-ethyl)-12-oxo-nonadec-4-enoate by LCMS, formic acid (5 mL) was added
  5. stirringthe mixture was stirred overnight
  6. distillationThe solvent was distilled off under reduced pressure
  7. additionTHF (5 mL) and a saturated aqueous solution (0.5 mL) of NaHCO3 were then added
  8. stirringthe mixture was stirred at room temperature for 10 minutes
  9. distillationThe solvent was distilled off under reduced pressure
  10. customThe residue was then purified by preparative HPLC
  11. customThe purified fraction was freeze-dried

Quellen und Nachweise

ORD-Eintrag
ord-e228825b333b476c83479e5345df7a41
Quelldatensatz
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09266853B2

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