Dicyclohexylcarbodiimide → HCID 67332263, Verbindung

HRID 1669219Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1669219
[O-:1][N+:2]1[C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][C:6]=2[N:5]=[C:4]([CH2:15][CH2:16][CH2:17][OH:18])[N:3]=1)[CH2:12][CH2:11][CH2:10]3.[C:19]([NH:26][C@H:27]([C:31](O)=[O:32])[CH:28]([CH3:30])[CH3:29])([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20].C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:22]([O:21][C:19]([NH:26][CH:27]([CH:28]([CH3:30])[CH3:29])[C:31]([O:18][CH2:17][CH2:16][CH2:15][C:4]1[N:3]=[N+:2]([O-:1])[C:7]2[CH:8]=[C:9]3[C:13]([CH2:12][CH2:11][CH2:10]3)=[CH:14][C:6]=2[N:5]=1)=[O:32])=[O:20])([CH3:25])([CH3:24])[CH3:23]

Komponenten

6

Edukt 3

HCID 10868DicyclohexylcarbodiimideHCID 83693Boc-L-ValineHCID 119516443-(1-Oxido-7,8-dihydro-6H-indeno[5,6-e][1,2,4]triazin-3-yl)-1-propanol

Produkt 1

HCID 67332263HCID 67332263, VerbindungAusbeute 94,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

A mixture of alcohol 70 (50 mg, 0.20 mmol), N-Boc Valine (44 mg, 0.20 mmol), DCC (46 mg, 0.22 mmol) and DMAP (2.5 mg, 0.02 mmol) in DCM (10 mL) was stirred at 20° C. for 1 h. The solvent was evaporated and the residue purified by chromatography, eluting with a gradient (0-5%) of MeOH/DCM, to give the crude ester, which was suspended in DCM (2 mL) and filtered to remove urea by-products. The filtrate was concentrated to give crude ester 310 (84 mg, 93%) as a pale-brown gum: 1H NMR δ 8.27 (s, 1H, H-9); 7.76 (s, 1H, H-5), 4.96-5.03 (m, 1H, CH), 4.28 (t, J=6.5 Hz, 2H, CH2O), 3.08-3.16 (m, 6H, H-6, H-8, CH2), 2.21-2.31 (m, 4H, H-7, CH2), 2.08-2.17 (br m, 1H, CH), 1.46 [s, 9H, C(CH3)3], 0.97 (d, J=6.9 Hz, 3H, CH3), 0.91 (d, J=6.9 Hz, 3H, CH3), NH not observed; HRMS calcd for C23H32N4O5 (M+) m/z 444.2373, found 444.2382.

Aufarbeitung

  1. customThe solvent was evaporated
  2. customthe residue purified by chromatography
  3. washeluting with a gradient (0-5%) of MeOH/DCM
  4. customto give the crude ester, which
  5. filtrationfiltered
  6. customto remove urea by-products
  7. concentrationThe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-1a2cf7b6b5aa49729295fc54f004bcbf
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07989451B2

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