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

HRID 2074350ノート

反応式

HRID 2074350 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-dc946ba0ec624df2b40f29c6ddf6ed62
出典データセット
uspto-grants-2011_04
特許番号
US07919468B2

反応ノート

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