Trifluoroacetic acid → HCID 58619083、化合物

HRID 1795179ノート

反応式

HRID 1795179 の反応式
[N:1]1([C:7]2([CH2:13][OH:14])[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:15]([O:19][C:20]([NH:22][C@H:23]([CH2:27][C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=1)[C:24](O)=[O:25])=[O:21])([CH3:18])([CH3:17])[CH3:16].ON1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC.C(N(CC)C(C)C)(C)C.FC(F)(F)C(O)=O>CN(C)C=O>[C:15]([O:19][C:20](=[O:21])[NH:22][C@H:23]([CH2:27][C:28]1[CH:29]=[CH:30][C:31]([Cl:34])=[CH:32][CH:33]=1)[C:24]([N:10]1[CH2:11][CH2:12][C:7]([CH2:13][OH:14])([N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[CH2:8][CH2:9]1)=[O:25])([CH3:18])([CH3:16])[CH3:17]

参加物

8

反応物 6

HCID 6422Trifluoroacetic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 7018791N-Boc-4-chloro-D-phenylalanineHCID 22185336HCID 22185336、化合物

生成物 1

HCID 58619083HCID 58619083、化合物収率 43%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

To a round bottom flask equipped with a stirring bar is charged [1,4′]bipiperidinyl-4′-yl-methanol, 22, (2.2 g, 11.1 mmol, 1.0 eq.) 2-(R)-tert-butoxycarbonylamino-3-(4-chlorophenyl)-propionic acid (3.648 g, 12.2 mmol), 1-hydroxybenzotriazole (2.552 g, 18.9 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (3.71 g, 18.9 mmol) in anhydrous N,N-dimethylformamide (80 mL). The mixture is cooled to 0° C. and N,N-diisopropyl-ethylamine (4.1 mL, 37.7 mmol) is added. The ice bath is removed and the reaction mixture allowed to stir overnight. The mixture is concentrated under reduced pressure and purified by preparative HPLC to afford 2.83 g (43% yield) of the desired compound as the trifluoroacetic acid salt. 1H NMR (CD3OD, 300 MHz) δ 0.85–2.13 (m, 19H), 2.65–3.82 (m, 8H), 3.90–4.10 (m, 3H), 4.48 (m, 1H), 4.76 (m, 1H), 7.22–7.48 (m, 4H). MS (ESI) m/z 480 (M+H+).

後処理

  1. customTo a round bottom flask equipped with a stirring bar
  2. customThe ice bath is removed
  3. concentrationThe mixture is concentrated under reduced pressure
  4. custompurified by preparative HPLC

出典と根拠

ORDレコード
ord-059dc44b6d694ad197435a022983b47a
出典データセット
uspto-grants-2006_04
特許番号
US07026335B2

反応ノート

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