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

HRID 2074363ノート

反応式

HRID 2074363 の反応式
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

参加物

7

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  1. customThe crude residue was chromatographed over silica gel

出典と根拠

ORDレコード
ord-6c8fbeff64a140e8b81693e0424dcca7
出典データセット
uspto-grants-2011_04
特許番号
US07919468B2

反応ノート

読み込み中…