Triethylamine → HCID 58609841、化合物

HRID 529985ノート

反応式

HRID 529985 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8](O)[C:9]1[S:13][C:12]([NH:14][C:15]([C:17]2([C:20]3[CH:28]=[CH:27][C:23]4[O:24][CH2:25][O:26][C:22]=4[CH:21]=3)[CH2:19][CH2:18]2)=[O:16])=[N:11][CH:10]=1.C(N(CC)CC)C.CS(Cl)(=O)=O.[NH:42]1[CH2:46][CH2:45][C@@H:44]([OH:47])[CH2:43]1>ClCCl>[O:24]1[C:23]2[CH:27]=[CH:28][C:20]([C:17]3([C:15]([NH:14][C:12]4[S:13][C:9]([CH:8]([C:3]5[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=5[Cl:1])[N:42]5[CH2:46][CH2:45][C@@H:44]([OH:47])[CH2:43]5)=[CH:10][N:11]=4)=[O:16])[CH2:18][CH2:19]3)=[CH:21][C:22]=2[O:26][CH2:25]1

参加物

6

反応物 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 2759337(R)-3-PyrrolidinolHCID 11774705HCID 11774705、化合物

生成物 1

HCID 58609841HCID 58609841、化合物収率 33,333.301%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

1-Benzo[1,3]dioxol-5-yl-cyclopropanecarboxylic acid [5-[(2-chloro-phenyl)-hydroxy-methyl]-thiazol-2-yl]-amide (0.500 g, 1.17 mmol) was placed in 10 mL of anhydrous dichloromethane containing trieihylamine (984 μL, 7.02 mmol). The mixture was cooled to 0° C. and methanesulfonyl chloride (364 μL, 4.68 mmol) was added, immediately followed by (R)-pyrrolidin-3-ol (945 μL, 11.7 mmol) and the solution was allowed to stir for 10 minutes at room temperature. The crude product was washed three times with an equal volume of a saturated aqueous solution of sodium bicarbonate, followed by a saturated aqueous solution of sodium chloride. The organic layer was then dried over sodium sulfate and evaporated to dryness. The crude mixture was purified by column, chromatography (20-90% ethyl acetate in hexanes on silica gel) to yield the product as a white solid (194.2 mg, 0.390 mol, 33.3%). 1H NMR (400 MHz, DMSO-d6) δ 1.09-1.15 (m, 2H), 1.41-1.44 (m, 2H), 1.54-1.63 (m, 1H), 1.93-2.77 (m, 5H), 4.20 (S, 1H), 4.72-4.77 (m, 1H), 4.96 (d, J=7.0 Hz, 1H), 6.00 (s, 2H), 6.85 (d, J=0.9 Hz, 2H), 6.95 (s, 1H), 7.24-7.29 (m, 1H), 7.37-7.43 (m, 3H), 7.76-7.80 (m, 1H), 11.03 (s, 1H. ESI-MS m/z calc. 497.1, found; 498.1 (M+1)+; Retention time 2.36 minutes.

後処理

  1. washThe crude product was washed three times with an equal volume of a saturated aqueous solution of sodium bicarbonate
  2. dry with materialThe organic layer was then dried over sodium sulfate
  3. customevaporated to dryness
  4. customThe crude mixture was purified by column, chromatography (20-90% ethyl acetate in hexanes on silica gel)

出典と根拠

ORDレコード
ord-6eea2faf49b64071ad849dab2245c49b
出典データセット
uspto-grants-2016_05
特許番号
US09351962B2

反応ノート

読み込み中…