Diisopropylethylamine → (2S,4R)-methyl 1-((2S,3R)-2-(tert-butoxycarbonylamino)-3-ethyl-5-methylnon-8-enoyl)-4-hydroxypyrrolidine-2-carboxylate

HRID 1852201Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1852201
[C:1]([O:5][C:6]([NH:8][CH:9]([C@H:13]([CH2:21][CH3:22])[CH2:14][CH:15]([CH3:20])[CH2:16][CH2:17][CH:18]=[CH2:19])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[OH:56][C@H:57]1[CH2:61][NH:60][C@H:59]([C:62]([O:64][CH3:65])=[O:63])[CH2:58]1>ClCCl>[C:1]([O:5][C:6]([NH:8][C@@H:9]([C@H:13]([CH2:21][CH3:22])[CH2:14][CH:15]([CH3:20])[CH2:16][CH2:17][CH:18]=[CH2:19])[C:10]([N:60]1[CH2:61][C@H:57]([OH:56])[CH2:58][C@H:59]1[C:62]([O:64][CH3:65])=[O:63])=[O:12])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 7015125(4R)-4-Hydroxy-L-proline methyl esterHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86683261(3R)-2-(tert-butoxycarbonylamino)-3-ethyl-5-methylnon-8-enoic acid

Produkt 1

HCID 86683260(2S,4R)-methyl 1-((2S,3R)-2-(tert-butoxycarbonylamino)-3-ethyl-5-methylnon-8-enoyl)-4-hydroxypyrrolidine-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of (3R)-2-(tert-butoxycarbonylamino)-3-ethyl-5-methylnon-8-enoic acid (2 g, 6.38 mmole) in dichloromethane (20 mL) was added DIPEA (1.93 mL, 19.19 mmole), HATU (2.42 g, 6.38 mmole) followed by (2S,4R)-methyl 4-hydroxypyrrolidine-2-carboxylate (1.15 g, 6.38 mmole) at room temperature. The reaction mixture was stirred at room temperature for 2 h. The reaction mass was diluted with DCM and washed with water. The organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure to get crude compound. The crude compound was taken to the next step without further purification (1.5 g, 53.4%). MS: MS m/z 441.6 (M++1)

Aufarbeitung

  1. washwashed with water
  2. dry with materialThe organic layer was dried over anhydrous Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customto get crude compound
  5. customThe crude compound was taken to the next step without further purification (1.5 g, 53.4%)

Quellen und Nachweise

ORD-Eintrag
ord-d9226276fdb4432091b80cb0dc1d0032
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08957203B2

Notizen zur Reaktion

Wird geladen…