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Diisopropylamine → 4-Fluorobenzenesulfonic acid 2-(2-methoxy-acetylamino)benzothiazol-6-yl ester

HRID 1867988
ノート
印刷プレビュー

反応式

HRID 1867988 の反応式
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][S:12]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[CH:8]=[CH:7][C:5]=2[N:6]=1.[CH3:22][O:23][CH2:24][C:25](O)=[O:26].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(NC(C)C)(C)C>CN(C)C=O.C(OCC)(=O)C.O>[CH3:22][O:23][CH2:24][C:25]([NH:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][S:12]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)(=[O:13])=[O:14])[CH:8]=[CH:7][C:5]=2[N:6]=1)=[O:26]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 7912DiisopropylamineHCID 12251Methoxyacetic AcidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 579808144-Fluorobenzenesulfonic acid 2-aminobenzothiazol-6-yl ester2 回

生成物 1

HCID 579808544-Fluorobenzenesulfonic acid 2-(2-methoxy-acetylamino)benzothiazol-6-yl ester
収率 72%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of 4-fluorobenzenesulfonic acid 2-aminobenzothiazol-6-yl ester (intermediate 16) (101.2 mg, 0.312 mmol), methoxyacetic acid (84.3 mg, 0.936 mmol), HBTU (355 mg, 0.936 mmol) and N,N-diisopropylamine (326 μl, 1.872 mmol) in 5 ml of dimethylformamide in a test tube, equipped with a magnetic bar, is stirred for 20 hours at room temperature. 100 ml of water are added and the reaction medium is extracted with ethyl acetate. The organic phase is dried over magnesium sulfate and evaporated. The residue obtained is taken up in ethyl acetate and purified on a Varian flash cartridge containing 5 g of silica of porosity 15-35μ, with a mixture of 1% methanol in dichloro-methane. After evaporating off the solvent, 89 mg of 4-fluorobenzenesulfonic acid 2-but-3-enoylaminobenzothiazol-6-yl ester are obtained (yellow oil) in a yield of 72%. LC/MS (method A1): [M+H]+: 397.11, retention time: 3.59 min.

後処理

  1. extractionthe reaction medium is extracted with ethyl acetate
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. customevaporated
  4. customThe residue obtained
  5. custompurified on a Varian flash cartridge
  6. additioncontaining 5 g of silica of porosity 15-35μ
  7. additionwith a mixture of 1% methanol in dichloro-methane
  8. customAfter evaporating off the solvent, 89 mg of 4-fluorobenzenesulfonic acid 2-but-3-enoylaminobenzothiazol-6-yl ester
  9. customare obtained (yellow oil) in a yield of 72%

出典と根拠

ORDレコード
ord-4feee44152e0407fb018768582c4aef1
出典データセット
uspto-grants-2009_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07632952B2

反応ノート

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