HCID 57654653、化合物 → HCID 57654650、化合物

HRID 1175129ノート

反応式

HRID 1175129 の反応式
[CH2:1]([O:3][C:4]([C:6]1[NH:7][N:8]=[C:9]2[C:18]3[C:13](=[CH:14][N:15]=[C:16]([Cl:19])[CH:17]=3)[CH2:12][CH2:11][C:10]=12)=[O:5])[CH3:2].O(C(C)(C)C)[Li].[C:26]([O:30][C:31]([N:33]1[CH2:36][C:35]([NH:43][C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])([CH2:37]OS(C)(=O)=O)[CH2:34]1)=[O:32])([CH3:29])([CH3:28])[CH3:27]>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:37][C:35]2([NH:43][C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[CH2:34][N:33]([C:31]([O:30][C:26]([CH3:27])([CH3:28])[CH3:29])=[O:32])[CH2:36]2)[N:8]=[C:9]2[C:18]3[C:13](=[CH:14][N:15]=[C:16]([Cl:19])[CH:17]=3)[CH2:12][CH2:11][C:10]=12)=[O:5])[CH3:2]

参加物

5

反応物 3

HCID 57654653HCID 57654653、化合物HCID 59558516HCID 59558516、化合物HCID 178506942HCID 178506942、化合物

生成物 1

HCID 57654650HCID 57654650、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

8-Chloro-4,5-dihydro-2H-1,2,7-triaza-cyclopenta[a]naphthalene-3-carboxylic acid ethyl ester (320 mg; 1.15 mmol) in DMF (4 ml) is treated at 5° C. with LiOtBu (1N in THF; 1.16 ml; 1.16 m mol) for 5 minutes. 3-tert-butoxycarbonylamino-3-methanesulfonyloxymethyl-azetidine-1-carboxylic acid tert-butyl ester (0.32 mg; 1.15 mmol) is added and the mixture heated to 90° C. for 30 minutes. The reaction mixture is poured on brine and extracted with TBME three times. The combined organic phases are dried over Na2SO4, evaporated to dryness and yield the title compound as colorless crystals. 1H-NMR (400 MHz; DMSO-d6: 8.38 (s, 1H); 7.65 (s, 1H); 7.42 (bs, 1H); 5.00 (bs, 2H); 4.34 (q, 2H); 4.03 (bd, 2H); 3.79 (m, 2H); 3.00 (m, 2H); 2.95 (m, 2H); 1.40 (s, 18H); 1.36 (t, 3H). MS (m/z) ES+: 562 (MH+).

後処理

  1. additionThe reaction mixture is poured on brine
  2. extractionextracted with TBME three times
  3. dry with materialThe combined organic phases are dried over Na2SO4
  4. customevaporated to dryness

出典と根拠

ORDレコード
ord-a3114a6d24574eb4bd05c95c22fe752e
出典データセット
uspto-grants-2010_11
特許番号
US07838674B2

反応ノート

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