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Triethylamine → Biphenyl-4-carboxylic acid (R)-(6-(1-((2-methoxyethyl)methylamino)ethylideneamino)-2(R)-hydroxyindan-1-yl)amide

HRID 2224738
ノート
印刷プレビュー

反応式

HRID 2224738 の反応式
[CH3:1][O:2][CH2:3][CH2:4][N:5]([CH3:20])[C:6](=[N:8][C:9]1[CH:17]=[C:16]2[C:12]([CH2:13][C@@H:14]([OH:19])[C@@H:15]2[NH-:18])=[CH:11][CH:10]=1)[CH3:7].C(OC(=O)N)(C)(C)C.C(N(CC)CC)C.O=C1CCC(=O)N1[O:43][C:44]([C:46]1[CH:51]=[CH:50][C:49]([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)=[CH:48][CH:47]=1)=O>C(O)(C(F)(F)F)=O.C(Cl)Cl>[CH3:1][O:2][CH2:3][CH2:4][N:5]([CH3:20])[C:6](=[N:8][C:9]1[CH:17]=[C:16]2[C:12]([CH2:13][C@@H:14]([OH:19])[C@@H:15]2[NH:18][C:44]([C:46]2[CH:51]=[CH:50][C:49]([C:52]3[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=3)=[CH:48][CH:47]=2)=[O:43])=[CH:11][CH:10]=1)[CH3:7]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 8471TriethylamineHCID 6847362,5-Dioxopyrrolidin-1-yl [1,1'-biphenyl]-4-carboxylateHCID 86607037carbamic acid tert-butyl ester (R)-(6-(1-((2-methoxyethyl)methylamino)ethylideneamino)-2(R)-hydroxyindan-1-yl)amide

生成物 1

HCID 9804160Biphenyl-4-carboxylic acid (R)-(6-(1-((2-methoxyethyl)methylamino)ethylideneamino)-2(R)-hydroxyindan-1-yl)amide収率 50.9%

試薬・触媒・溶媒 2

HCID 6344
Dichloromethane
溶媒
HCID 6422Trifluoroacetic acid溶媒

実験手順

Dissolve carbamic acid tert-butyl ester (R)-(6-(1-((2-methoxyethyl)methylamino)ethylideneamino)-2(R)-hydroxyindan-1-yl)amide (153.6 mg, 0.407 mmol) in excess TFA at 0° C. and allow to stir for 1 hour. Remove the solvent in vacuo. Dissolve the residue in 10 mL methylene chloride and add triethylamine (411.8 mg, 4.07 mmol) and biphenyl-4-carboxylic acid 2,5-dioxopyrrolidin-1-yl ester (118.3 mg, 0.400 mmol). Allow the reaction mixture to stir for 21 hours. Dilute the reaction mixture with methylene chloride and wash it with saturated aqueous sodium hydrogen carbonate (1×) and brine (1×). Dry the organic layer with magnesium sulfate. Filter and remove the solvent in vacuo to give 162.1 mg of crude product. Purify via Biotage chromatography (30% MeOH/EtOAc) to afford 93.1 mg of the titled product as an oil (50% yield). MS (ES): m/z 458.3(M+H).

後処理

  1. customRemove the solvent in vacuo
  2. dissolutionDissolve the residue in 10 mL methylene chloride
  3. stirringto stir for 21 hours
  4. washwash it with saturated aqueous sodium hydrogen carbonate (1×) and brine (1×)
  5. dry with materialDry the organic layer with magnesium sulfate
  6. filtrationFilter
  7. customremove the solvent in vacuo
  8. customto give 162.1 mg of crude product
  9. customPurify via Biotage chromatography (30% MeOH/EtOAc)

出典と根拠

ORDレコード
ord-593ec59d33854cd781be148627bb5bca
出典データセット
uspto-grants-2008_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07378447B2

反応ノート

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