Lithium Hydroxide → N-Boc-Tyr(Bn)-Leu-OH

HRID 2074350Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2074350
[NH:1]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[C@H:2]([C:18]([NH:20][C@H:21]([C:26]([O:28]C)=[O:27])[CH2:22][CH:23]([CH3:25])[CH3:24])=[O:19])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][CH:5]=1.[Li+].[OH-]>C1COCC1>[NH:1]([C:30]([O:32][C:33]([CH3:35])([CH3:34])[CH3:36])=[O:31])[C@H:2]([C:18]([NH:20][C@H:21]([C:26]([OH:28])=[O:27])[CH2:22][CH:23]([CH3:25])[CH3:24])=[O:19])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][CH:5]=1

Komponenten

4

Edukt 2

HCID 3939Lithium HydroxideHCID 11283399Boc-Tyr(Bzl)-Leu-OMe

Produkt 1

HCID 57611771N-Boc-Tyr(Bn)-Leu-OH

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Same procedure as above with N-Boc-Tyr(Bn)-Leu-OMe (1.034 g, 2.073 mmol), aqueous LiOH (1 M, 2.2 mL, 2.2 mmol) in THF (15 mL). A white solid was obtained (1.035 g, 100%) which was used in the next step without further purification. 1H NMR (300 MHz, CDCl3) δ 0.90 (d, J=5 Hz, 1H, Me2 Leu), 1.40 (s, 9H, (CH3)3), 1.60 (m, 3H, CH2—CH Leu), 3.00 (m, 2H, CH2), 4.29 (m, 1H, CHα), 4.44 (m, 1H, CHα), 4.88 (s, 2H, CH2 (Bn)), 5.29 (broad s, 1H, NHBoc), 6.70 (m, 1H, NH amide), 6.91 (d, J=5 Hz, 2 aromatic H), 7.12 (d, J=5 Hz, 2 aromatic H), 7.33-7.44 (m, 5 aromatic H). 3C NMR (75 MHz, CDCl3) δ 21.8, 22.9, 24.7 (CH-Me2 Leu), 28.2 ((CH3)3), 37.0 CH2 Leu), 41.1 (CH2 Tyr), 51.6 (CHα Leu), 55.7 (CHα Tyr), 70 (CH2 (Bn)), 80.4 (C(CH3)3), 114.9, 127.5, 127.9, 128.5, 128.9, 130.5, 137.0 (11 aromatic C), 155.8, 157.8 (Car-O, CO carbamate), 172.0, 176.8 (CO acid, CO amide).

Aufarbeitung

  1. customA white solid was obtained (1.035 g, 100%) which
  2. customwas used in the next step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-dc946ba0ec624df2b40f29c6ddf6ed62
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07919468B2

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