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Tetrahydrofuran → (2S,4R)-1-(1-carbamoyl-1H-indol-3-ylcarbamoyl)-4-fluoro-pyrrolidine-2-carboxylic acid benzyl ester

HRID 1527377
ノート
印刷プレビュー

反応式

HRID 1527377 の反応式
OC(C(F)(F)F)=O.[CH2:8]([O:15][C:16]([C@@H:18]1[CH2:22][C@@H:21]([F:23])[CH2:20][NH:19]1)=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[N:24]([C:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[N:29]([C:36]([NH2:38])=[O:37])[CH:28]=1)=[C:25]=[O:26].C1COCC1.C(N(CC)CC)C>O>[CH2:8]([O:15][C:16]([C@@H:18]1[CH2:22][C@@H:21]([F:23])[CH2:20][N:19]1[C:25](=[O:26])[NH:24][C:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[N:29]([C:36](=[O:37])[NH2:38])[CH:28]=1)=[O:17])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1
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 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 575200853-Isocyanato-indole-1-carboxylic acid amideHCID 131733200(2S,4R)-4-fluoro-pyrrolidine-2-carboxylic acid benzyl ester TFA salt

生成物 1

HCID 68283894(2S,4R)-1-(1-carbamoyl-1H-indol-3-ylcarbamoyl)-4-fluoro-pyrrolidine-2-carboxylic acid benzyl ester

試薬・触媒・溶媒 1

HCID 962
Water
溶媒

実験手順

To a solution of (2S,4R)-4-fluoro-pyrrolidine-2-carboxylic acid benzyl ester TFA salt (4.45 g, 13.2 mmol), 3-isocyanato-indole-1-carboxylic acid amide (2.65 g, 13.2 mmol) (prepared as described in Scheme A1) and THF (66 mL) was added triethylamine (5.51 mL, 39.6 mmol). The resulting solution was stirred at RT under nitrogen for 1 h until completion of the reaction. The mixture was poured in water and extracted with EtOAc. The organic layer was washed with an aqueous saturated solution of NaHCO3, dried over Na2SO4, filtered and concentrated. The crude material was purified by flash column chromatography on silica gel (c-hexane/EtOAc 9:1 to pure EtOAc) to give the desired compound. TLC, Rf (CH2Cl2/MeOH 9:1)=0.40; MS: 425.2 [M+H]+; tR (HPLC conditions a): 3.6 min.

後処理

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with an aqueous saturated solution of NaHCO3
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified by flash column chromatography on silica gel (c-hexane/EtOAc 9:1 to pure EtOAc)

出典と根拠

ORDレコード
ord-2501bf94a0854a1d849c33a6cdf8d32e
出典データセット
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09085555B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート