1,2-Dichloroethane → N-Boc-Tyr(Bn)-Asn-Trp-NHPh

HRID 2074354ノート

反応式

HRID 2074354 の反応式
[NH2:1][C@H:2]([C:13]([NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[NH:22]([C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])[C@H:23]([C:39]([NH:41][C@H:42]([C:47](O)=[O:48])[CH2:43][C:44](=[O:46])[NH2:45])=[O:40])[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:27][CH:26]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl.CN(C=O)C>[NH:22]([C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])[C@H:23]([C:39]([NH:41][C@H:42]([C:47]([NH:1][C@H:2]([C:13]([NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1)=[O:48])[CH2:43][C:44](=[O:46])[NH2:45])=[O:40])[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:27][CH:26]=1

参加物

6

反応物 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 16735217(S)-2-Amino-3-(1H-indol-3-yl)-N-phenylpropanamideHCID 57611773N-Boc-Tyr(Bn)-Asn-OH

生成物 1

HCID 16735715N-Boc-Tyr(Bn)-Asn-Trp-NHPh収率 30.1%

試薬・触媒・溶媒 1

HCID 22350042dichloromethane N,N-dimethylformamide溶媒

実験手順

compound SP314C2. Same procedure as above with Trp-NHPh (102.9 mg, 0.368 mmol), N-Boc-Tyr(Bn)-Asn-OH (178.9 mg, 0.368 mmol), EDC (78.2 mg, 0.41 mmol) and HOBt (55 mg, 0.41 mmol) in CH2Cl2/DMF (1.5 mL, 1/1). The crude residue was purified by flash column chromatography on silica gel (0-5% MeOH/CH2Cl2) to give an off-white solid (82.8 mg, 30%). 1H NMR (300 MHz, DMSO-d6) δ 1.28 (s, 9H, (CH3)3), 2.57-3.26 (m, 6H, CH2 Tyr, CH2 Trp, CH2 Asn), 4.11 (m, 1H, CHα), 4.58 (m, 2H, 2 CHα), 5.03 (broad s, 2H, CH2 (Bn)), 6.86-7.65 (m, 22H), 8.2 (m, 2H), 9.82 (s, 1H), 10.78 (s, 1H). 13C NMR (75 MHz, DMSO-d6) δ 27.3 (CH2 Trp), 28.1 ((CH3)3), 36.4, 37 (CH2 Tyr, CH2 Asn), 49.5, 54.5, 55.7 (CHα Tyr, Asn, Trp), 69 (CH2 (Bn)), 78.1 (C(CH3)3), 109.7, 110, 111.2, 114.2, 118.2, 119.6, 120.8, 123.4, 123.6, 127.2, 127.5, 127.7, 128.3, 128.5, 130.1, 136, 137.2, 138.7 (25 aromatic C), 155.2, 156.8 (Car-O, CO carbamate), 170, 171, 171.7, 171.9 (4 CO amide). Anal. Calcd. for C42H46N6O7: C, 67.54; H, 6.21; N, 11.25. Found: C, 67.14; H, 6.27; N, 11.27.

後処理

  1. customThe crude residue was purified by flash column chromatography on silica gel (0-5% MeOH/CH2Cl2)

出典と根拠

ORDレコード
ord-0f4955c96ad64de48e4ec0aa5bce6d20
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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