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Tetrahydrofuran → [2-(1H-Indol-3-yl)-2-oxo-ethyl]-carbamic Acid 3-(3-methyl-but-2-enylcarbamoyl)-2-oxo-2,3-dihydro-thiazol-5-yl Ester

HRID 583784
ノート
印刷プレビュー

反応式

HRID 583784 の反応式
[CH3:1][C:2]([CH3:15])=[CH:3][CH2:4][NH:5][C:6]([N:8]1[C:12](=O)[CH2:11][S:10][C:9]1=[O:14])=[O:7].[H-].[Na+].C(OC([N:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:27]([C:34](=[O:39])[CH2:35][N:36]=[C:37]=[O:38])=[CH:26]1)=O)(C)(C)C.C1C[O:43]CC1>>[CH3:1][C:2]([CH3:15])=[CH:3][CH2:4][NH:5][C:6]([N:8]1[CH:12]=[C:11]([O:43][C:37](=[O:38])[NH:36][CH2:35][C:34]([C:27]2[C:28]3[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=3)[NH:25][CH:26]=2)=[O:39])[S:10][C:9]1=[O:14])=[O:7]
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 4

HCID 8028Tetrahydrofuran2 回HCID 24758Sodium hydrideHCID 223425403-(3-Methyl-but-2-en-1-yl)aminocarbonyl-2,4-thiazolidinedioneHCID 223425462-(1-Tert-butoxycarbonyl-indol-3-yl)-2-oxo-ethylisocyanate

生成物 1

HCID 10127184[2-(1H-Indol-3-yl)-2-oxo-ethyl]-carbamic Acid 3-(3-methyl-but-2-enylcarbamoyl)-2-oxo-2,3-dihydro-thiazol-5-yl Ester

実験手順

To a stirred solution of 3-(3-methyl-but-2-en-1-yl)aminocarbonyl-2,4-thiazolidinedione (0.01 mol), which may be prepared as described in Step (a) above, in a solvent such as, for example, THF is added 1 mol equivalent of a non-nucleophilic base such as described in Step (f) above, preferably sodium hydride, and the mixture is stirred for from 1 minute to about 1 hour. To the mixture is added a solution of 2-(1-tert-butoxycarbonyl-indol-3-yl)-2-oxo-ethylisocyanate (0.01 mol), which may be prepared as described in Step (f) above, in a solvent such as, for example, THF. Reaction progress may be followed by TLC or HPLC. When a sufficient amount of desired product is formed, the mixture is partitioned between ethyl acetate and water, or optionally the mixture is first rotary evaporated, and the residue is so partitioned. The organic layer is washed with 0.01 M hydrochloric acid, water, brine, and dried over sodium sulfate. The mixture is rotary evaporated to give 2-[1-(tert-butoxycarbonyl)-indol-3-yl)-2-oxo-ethyl]carbamic acid, [3-(3-methyl-but-2-en-1-yl)aminocarbonyl-2,3-dihydrothiazol-2-on-5-yl] ester, which may be purified, if needed or desired, by chromatography on silica gel or crystallization.

後処理

  1. additionis added 1 mol equivalent of a non-nucleophilic base such
  2. custommay be prepared
  3. customReaction progress

出典と根拠

ORDレコード
ord-463bbc25b19f4bf793081c9962c7e8b7
出典データセット
uspto-grants-2005_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06924276B2

反応ノート

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