Triethylamine → t-Butyl (2-(5-bromo-1-((5-chlorothiazol-2-yl)carbamoyl)spiro[indoline-3,3'-pyrrolidin]-1'-yl)-2-oxoethyl)carbamate

HRID 1411235ノート

反応式

HRID 1411235 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:10]3([CH2:14][CH2:13][NH:12][CH2:11]3)[CH2:9][N:8]([C:15]([NH:17][C:18]3[S:19][C:20]([Cl:23])=[CH:21][N:22]=3)=[O:16])[C:5]2=[CH:6][CH:7]=1.C(N(CC)CC)C.[C:31]([NH:38][CH2:39][C:40](O)=[O:41])([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32].Cl.C(N=C=NCCCN(C)C)C>C(Cl)Cl.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:10]3([CH2:14][CH2:13][N:12]([C:40](=[O:41])[CH2:39][NH:38][C:31](=[O:32])[O:33][C:34]([CH3:35])([CH3:36])[CH3:37])[CH2:11]3)[CH2:9][N:8]([C:15](=[O:16])[NH:17][C:18]3[S:19][C:20]([Cl:23])=[CH:21][N:22]=3)[C:5]2=[CH:6][CH:7]=1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 78288N-(tert-butoxycarbonyl)glycineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 71522964HCID 71522964、化合物

生成物 1

HCID 117650996t-Butyl (2-(5-bromo-1-((5-chlorothiazol-2-yl)carbamoyl)spiro[indoline-3,3'-pyrrolidin]-1'-yl)-2-oxoethyl)carbamate収率 40%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

The 5-bromo-N-(5-chlorothiazol-2-yl)spiro[indoline-3,3′-pyrrolidine]-1-carboxamide (40 mg, 0.097 mmol) obtained in Example 2 was dissolved in methylene chloride (1.0 mL). Thereafter, triethylamine (27.0 μL, 0.194 mmol), N-Boc glycine (20 mg, 0.116 mmol), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (22 mg, 0.116 mmol) were added to the above obtained solution at room temperature, and the obtained mixture was then stirred for 12 hours. Thereafter, the reaction solution was diluted with water, and was then extracted with chloroform. The resultant was dried over anhydrous sodium sulfate and was then concentrated in vacuo. The obtained residue was purified by silica gel column chromatography (chloroform:methanol=10:1) to obtain the captioned compound (22.0 mg, 40%) in the form of a white solid.

後処理

  1. extractionwas then extracted with chloroform
  2. dry with materialThe resultant was dried over anhydrous sodium sulfate
  3. concentrationwas then concentrated in vacuo
  4. customThe obtained residue was purified by silica gel column chromatography (chloroform:methanol=10:1)

出典と根拠

ORDレコード
ord-a8af7786c06e47579e5307ffdf71bb70
出典データセット
uspto-grants-2014_12
特許番号
US08921576B2

反応ノート

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