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

HRID 2074350노트

반응식

HRID 2074350 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-dc946ba0ec624df2b40f29c6ddf6ed62
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07919468B2

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