N-Boc-Tyr(Bn)-Ala-Trp-OMe → N-Boc-Tyr-Ala-Trp-OMe

HRID 2074364ノート

反応式

HRID 2074364 の反応式
[NH:1]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[C@H:2]([C:18]([NH:20][C@H:21]([C:23]([NH:25][C@H:26]([C:37]([O:39][CH3:40])=[O:38])[CH2:27][C:28]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[NH:30][CH:29]=1)=[O:24])[CH3:22])=[O:19])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10]CC2C=CC=CC=2)=[CH:6][CH:5]=1>CO.[Pd]>[NH:1]([C:41]([O:43][C:44]([CH3:45])([CH3:47])[CH3:46])=[O:42])[C@H:2]([C:18]([NH:20][C@H:21]([C:23]([NH:25][C@H:26]([C:37]([O:39][CH3:40])=[O:38])[CH2:27][C:28]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[NH:30][CH:29]=1)=[O:24])[CH3:22])=[O:19])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1

参加物

4

反応物 1

HCID 44424692N-Boc-Tyr(Bn)-Ala-Trp-OMe

生成物 1

HCID 44424693N-Boc-Tyr-Ala-Trp-OMe収率 76%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

compound NR40. N-Boc-Tyr(Bn)-Ala-Trp-OMe (119 mg, 0.185 mmol) in solution in MeOH (4 mL) was hydrogenated overnight at atmospheric pressure in the presence of 10% Pd on charcoal (30 mg). After filtration, evaporation of the solvent and trituration with ether, N-Boc-Tyr-Ala-Trp-OMe (77 mg, 76%) was obtained as a solid. 1H NMR (300 MHz, DMSO-d6) δ 1.19 (d, J=7 Hz, 3H, CH3), 1.29 (s, 9H, (CH3)3), 2.55 and 2.80 (ABX system, 2H, CH2β), 3.13 and 3.16 (ABX system, 2H, CH2β), 3.55 (s, 3H, OCH3), 4.05 (m, 1H, CHα), 4.35 (m, 1H, CHα), 4.50 (m, 1H, CHα), 6.63 (d, J=8.3 Hz, 2H), 6.83 (d, J=8.6 Hz, 1H), 7.03 (m, 4H), 7.16 (d, J=2.1 Hz, 1H), 7.34 (d, J=7.9 Hz, 1H), 7.47 (d, J=7.8 Hz, 1H), 7.92 (d, J=7.4 Hz, 1H, NH), 8.32 (d, J=7.3 Hz, 1H, NH), 9.14 (s, 1H, OH), 10.86 (s, 1NH). 13C NMR (75 MHz, DMSO-d6) δ 18.4 (CH3); 26.9 (CH2 Trp), 28.1 ((CH3)3), 36.4 (CH2 Tyr), 47.8, 51.7, 53.0, 55.9 (CHα Ala, Tyr, Trp or OCH3), 77.9 (C(CH3)3), 109.1 (aromatic C), 111.4, 114.8, 117.9, 118.4, 120.9, 123.7 (aromatic CH), 127.0, 128.2 (aromatic C), 130.0 (aromatic CH), 136.0 (aromatic C), 155.2, 156.6 (Car-O or CO carbamate), 171.4, 172.0, 172.2 (2 CO amide or CO ester). Anal. Calcd. for C29H36N4O7, 1H2O: C, 61.04; H, 6.71; N, 9.82. Found: C, 61.02; H, 6.62; N, 9.66. HRMS (ESI) calcd for C29H36N4O7Na [(M+Na)+] 575.2482. Found 575.2480.

後処理

  1. filtrationAfter filtration, evaporation of the solvent and trituration with ether

出典と根拠

ORDレコード
ord-558366cbd7d44002b45fa081515c7a4a
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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