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

HRID 2074363노트

반응식

HRID 2074363 반응식
Cl.[NH2:2][C@H:3]([C:14]([O:16][CH3:17])=[O:15])[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1.[NH:18]([C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[C@H:19]([C:35]([NH:37][C@H:38]([C:40](O)=[O:41])[CH3:39])=[O:36])[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:23][CH:22]=1.C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1>C1COCC1>[NH:18]([C:43]([O:45][C:46]([CH3:47])([CH3:49])[CH3:48])=[O:44])[C@H:19]([C:35]([NH:37][C@H:38]([C:40]([NH:2][C@H:3]([C:14]([O:16][CH3:17])=[O:15])[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1)=[O:41])[CH3:39])=[O:36])[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:23][CH:22]=1

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 77980L-Tryptophan, methyl esterHCID 57611766N-Boc-Tyr(Bn)-Ala-OH

생성물 1

HCID 44424692N-Boc-Tyr(Bn)-Ala-Trp-OMe수율 56.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

compound NR36. Same procedure as above with HCl, Trp-OCH3 (255 mg, 1 mmol), N-Boc-Tyr(Bn)-Ala-OH (444 mg, 1 mmol), DCC (259 mg, 1.26 mmol) and HOBt (172 mg, 1.27 mmol) in THF (15 mL). The crude residue was chromatographed over silica gel to afford a white solid (361 mg, 56%). 1H NMR (300 MHz, DMSO-d6) δ 1.22 (d, J=7 Hz, 3H, CH3), 1.29 (s, 9H, (CH3)3), 2.62 and 2.92 (ABX system, 2H, CH2P), 3.08 and 3.13 (ABX system, 2H, CH2β) 3.55 (s, 3H, OCH3), 4.10 (m, 1H, CHα), 4.36 (m, 1H, CHα), 4.49 (m, 1H, CHα), 5.03 (s, 2H, CH2 (OBn)), 6.85-7.50 (m, 15H, 14 aromatic H+1 NH), 7.97 (d, J=7.3 Hz, 1H), 8.34 (d, J=7.0 Hz, 1H), 10.88 (s, 1NH). 13C NMR (75 MHz, DMSO-d6) δ 18.2 (CH3), 26.8 (CH2 Trp), 28.0 ((CH3)3), 36.3 (CH2 Tyr), 47.6, 51.6, 53.0, 55.6 (CHα Ala, Tyr, Trp or OCH3), 69 (CH2 (OBn)), 77.9 (C(CH3)3), 109.0 (aromatic C), 111.2, 114.2, 117.8, 118.3, 120.8, 123.6 (aromatic CH), 126.9 (aromatic C), 127.4, 127.6, 128.2, 130.0 (aromatic CH), 130.2, 135.9, 137.1 (aromatic C), 155.1, 156.7 (Car-O or CO carbamate), 171.2, 171.9, 172.1 (2 CO amide or CO ester). Anal. Calcd. for C36H42N4O7, 0.5H2O: C, 66.34; H, 6.65; N, 8.60. Found: C, 66.29; H, 6.64; N, 8.48.

후처리

  1. customThe crude residue was chromatographed over silica gel

출처 및 근거

ORD 기록
ord-6c8fbeff64a140e8b81693e0424dcca7
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07919468B2

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