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

HRID 2074364노트

반응식

HRID 2074364 반응식
[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

참가 물질

4

반응물 1

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

생성물 1

HCID 44424693N-Boc-Tyr-Ala-Trp-OMe수율 76%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-558366cbd7d44002b45fa081515c7a4a
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07919468B2

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