Diisopropylethylamine → (2S,4R)-methyl 1-((2S,3S)-2-((tert-butoxycarbonyl)amino)-3-((R)-hex-5-en-2-yloxy)pentanoyl)-4-hydroxypyrrolidine-2-carboxylate

HRID 523179

Reaktionsgleichung

Reaktionsgleichung von HRID 523179
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C@@H:13]([O:16][C@@H:17]([CH2:19][CH2:20][CH:21]=[CH2:22])[CH3:18])[CH2:14][CH3:15])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[OH:24][C@H:25]1[CH2:29][NH:28][C@H:27]([C:30]([O:32][CH3:33])=[O:31])[CH2:26]1.F[P-](F)(F)(F)(F)F.CN(C(N(C)C)=[N+]1C2C(=NC=CC=2)[N+]([O-])=N1)C.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[C:1]([O:5][C:6]([NH:8][C@@H:9]([C@@H:13]([O:16][C@@H:17]([CH2:19][CH2:20][CH:21]=[CH2:22])[CH3:18])[CH2:14][CH3:15])[C:10]([N:28]1[CH2:29][C@H:25]([OH:24])[CH2:26][C@H:27]1[C:30]([O:32][CH3:33])=[O:31])=[O:12])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 114353194-Hydroxy-L-proline methyl ester hydrochlorideHCID 90118157(2S,3S)-2-((tert-butoxycarbonyl)amino)-3-((R)-hex-5-en-2-yloxy)pentanoic acid2×HCID 178484293HCID 178484293, Verbindung

Produkt 1

HCID 90117961(2S,4R)-methyl 1-((2S,3S)-2-((tert-butoxycarbonyl)amino)-3-((R)-hex-5-en-2-yloxy)pentanoyl)-4-hydroxypyrrolidine-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a round-bottom flask equipped with a stir bar was added (2S,3S)-2-((tert-butoxycarbonyl)amino)-3-(pent-4-en-1-yloxy)pentanoic acid (all material from step 1, 438 mg, 1.39 mmol), (2S,4R)-methyl 4-hydroxypyrrolidine-2-carboxylate-HCl salt (277 mg, 1.53 mmol), 1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (“HATU”, 528 mg, 1.39 mmol), and CH2Cl2 (10 mL). To the mixture was added N,N-diisopropylethylamine (0.728 mL, 4.17 mmol). The mixture was stirred at room temperature for 16 h. The reaction mixture was transferred to a separatory funnel and was thrice washed with aq. 1N HCl; then brine. The organic phase was dried over MgSO4; filtered; then concentrated in vacuo to afford (2S,4R)-methyl 1-((2S,3S)-2-((tert-butoxycarbonyl)amino)-3-((R)-hex-5-en-2-yloxy)pentanoyl)-4-hydroxypyrrolidine-2-carboxylate as a yellow oil.

Aufarbeitung

  1. customTo a round-bottom flask equipped with a stir bar
  2. customThe reaction mixture was transferred to a separatory funnel
  3. washwashed with aq. 1N HCl
  4. dry with materialThe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. concentrationthen concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-11e958c28829450f87dd608a06681fe6
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09334279B2

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