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Isobutyl chloroformate → Ammonia

HRID 571360
ノート
印刷プレビュー

反応式

HRID 571360 の反応式
[CH3:1][O:2][C@H:3]1[C@@H:8]([NH:9][C@@H:10]2[CH2:17][C@H:13]3[CH2:14][NH:15][CH2:16][C@@:12]3([C:18]([N:20]3[CH2:29][CH2:28][C:27]4[N:26]=[CH:25][C:24]([C:30]([F:33])([F:32])[F:31])=[CH:23][C:22]=4[CH2:21]3)=[O:19])[CH2:11]2)[CH2:7][CH2:6][O:5][CH2:4]1.Cl[C:35]([O:37][CH2:38][CH:39]([CH3:41])[CH3:40])=[O:36]>C(Cl)Cl>[NH3:9].[CH3:1][O:2][C@H:3]1[C@@H:8]([NH:9][C@@H:10]2[CH2:17][C@H:13]3[CH2:14][N:15]([C:35]([O:37][CH2:38][CH:39]([CH3:41])[CH3:40])=[O:36])[CH2:16][C@@:12]3([C:18]([N:20]3[CH2:29][CH2:28][C:27]4[N:26]=[CH:25][C:24]([C:30]([F:33])([F:31])[F:32])=[CH:23][C:22]=4[CH2:21]3)=[O:19])[CH2:11]2)[CH2:7][CH2:6][O:5][CH2:4]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 62365Isobutyl chloroformateHCID 86708896((3aR,5R,6aR)-5-(((3S*,4S*)-3-Methoxytetrahydro-2H-pyran-4-yl)amino)octahydro-cyclopenta[c]pyrrol-3a-yl)(3-(trifluoromethyl)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl)methanone

生成物 2

HCID 222Ammonia収率 5%HCID 89928869(3aR,5R,6aR)-Isobutyl 5-(((3S*,4S*)-3-methoxytetrahydro-2H-pyran-4-yl)amino)-3a-(3-(trifluoromethyl)-5,6,7,8-tetrahydro-1,6-naphthyridine-6-carbonyl)hexahydro-cyclopenta[c]pyrrole-2(1H)-carboxylate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a solution of Example 1 (0.1 g, 0.213 mmol) and TEA (0.12 mL, 0.854 mmol) in DCM (2.6 mL) at 0° C. was added isobutyl chloroformate (0.086 mL, 0.64 mmol). The mixture was stirred at 0° C. for 30 min and at rt overnight. The reaction was quenched by addition of saturated aqueous NaHCO3 solution, extracted with DCM, dried over Na2SO4. Purification by CombiFlash (eluent: 5% methanol in DCM, then 5% 7N NH3 in methanol in DCM) gave the title compound as a white solid. 1H-NMR (400 MHz, CDCl3): δ 0.93 (d, J=6.3 Hz, 6H), 1.57-1.99 (m, 7H), 2.32 (br. s., 1H), 2.74 (br. s., 1H), 3.08-3.56 (m, 10H), 3.56-4.00 (m, 9H), 4.01-4.11 (m, 1H), 4.57-5.07 (m, 2H), 7.70 (br. s., 1H), 8.72 (br. s., 1H); LC/MS: C28H39F3N4O5: m/z 569.3 (M+H).

後処理

  1. customThe reaction was quenched by addition of saturated aqueous NaHCO3 solution
  2. extractionextracted with DCM
  3. dry with materialdried over Na2SO4
  4. customPurification by CombiFlash (eluent

出典と根拠

ORDレコード
ord-338c89807cca45ddbb0f1e44ac147e69
出典データセット
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09024017B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート