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Triethylamine → 5-(4-Benzothiazol-2-ylmethyl-benzyl)-2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester

HRID 384506
ノート
印刷プレビュー

反応式

HRID 384506 の反応式
Cl[CH2:2][C:3]1[CH:18]=[CH:17][C:6]([CH2:7][C:8]2[S:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:5][CH:4]=1.[C:19]([O:23][C:24]([N:26]1[CH2:31][C@@H:30]2[CH2:32][C@H:27]1[CH2:28][NH:29]2)=[O:25])([CH3:22])([CH3:21])[CH3:20].CCN(CC)CC>CC#N>[C:19]([O:23][C:24]([N:26]1[CH2:31][CH:30]2[CH2:32][CH:27]1[CH2:28][N:29]2[CH2:2][C:3]1[CH:18]=[CH:17][C:6]([CH2:7][C:8]2[S:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:5][CH:4]=1)=[O:25])([CH3:22])([CH3:20])[CH3:21]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 8471TriethylamineHCID 11521263(1S,4S)-2-Boc-2,5-diazabicyclo[2.2.1]heptaneHCID 672064032-(4-Chloromethyl-benzyl)-benzothiazole

生成物 1

HCID 672064685-(4-Benzothiazol-2-ylmethyl-benzyl)-2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester収率 55%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a solution of 2-(4-chloromethyl-benzyl)-benzothiazole (1.0 g, 3.7 mmol) and (S,S)-2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester (0.9 g, 4.4 mmol) in CH3CN (36 mL) was added Et3N (0.77 mL, 5.5 mmol) and the resulting solution was stirred at rt for 24 h. The reaction mixture was then concentrated and the crude residue was then partitioned between CH2Cl2 (200 mL) and satd. aq. NaHCO3 (200 mL). The organic layer was separated, dried (MgSO4), filtered and concentrated. Purification by silica gel flash chromatography (0% to 10% CH3OH in CH2Cl2) afforded the title compound as clear oil (0.88 g, 55%). MS (ESI): mass calcd. for C25H29N3O2S, 435.59; m/z found, 436.2 [M+H]+. 1H NMR (500 MHz, CDCl3, mixture of rotamers): 8.01 (d, J=8.2 Hz, 1H), 7.81 (d, J=8.0 Hz, 1H), 7.48-7.45 (m, 1H), 7.37-7.34 (m, 5H), 4.44 (s, 2H), 4.40 (br s, 0.5H), 4.25 (br s, 0.5H), 3.75-3.75 (m, 2H), 3.64-3.44 (m, 2H), 3.17 (t, J=11.3 Hz, 1H), 2.90 (dd, J=25.2, 9.5 Hz, 1H), 2.74 (d, J=9.6 Hz, 0.5H), 2.55 (d, J=9.4 Hz, 0.5H), 1.88-1.86 (br m, 1H), 1.73-1.65 (br m, 1H), 1.48 (s, 9H).

後処理

  1. concentrationThe reaction mixture was then concentrated
  2. customthe crude residue was then partitioned between CH2Cl2 (200 mL)
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by silica gel flash chromatography (0% to 10% CH3OH in CH2Cl2)

出典と根拠

ORDレコード
ord-203428f231ce4002bde95cca723e7dce
出典データセット
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08367719B2

反応ノート

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