Diisopropylethylamine → (R)-Methyl 3-(2-tert-butylbenzamido)-2,3-dihydro-1H-indene-5-carboxylate

HRID 1193270ノート

反応式

HRID 1193270 の反応式
[C:1]([C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([OH:9])=O)([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[NH2:47][C@H:48]1[C:56]2[C:51](=[CH:52][CH:53]=[C:54]([C:57]([O:59][CH3:60])=[O:58])[CH:55]=2)[CH2:50][CH2:49]1>ClCCl>[C:1]([C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([NH:47][C@H:48]1[C:56]2[C:51](=[CH:52][CH:53]=[C:54]([C:57]([O:59][CH3:60])=[O:58])[CH:55]=2)[CH2:50][CH2:49]1)=[O:9])([CH3:2])([CH3:3])[CH3:4]

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 136850tert-Butylbenzoic acid (mixed isomers)HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 55278060(R)-Methyl 3-amino-2,3-dihydro-1H-indene-5-carboxylate

生成物 1

HCID 66798706(R)-Methyl 3-(2-tert-butylbenzamido)-2,3-dihydro-1H-indene-5-carboxylate収率 57%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

実験手順

2-tert-Butylbenzoic acid (0.75 g, 4.2 mmol, 1 eq) was dissolved in dichloromethane (40 ml), and at 0° C. HATU (1.5 g, 4.2 mmol, 1 eq) and DIPEA (1.7 ml, 10.52 mmol, 2.5 eq) were added and stirring was carried out for 30 min. Then (R)-methyl 3-amino-2,3-dihydro-1H-indene-5-carboxylate (A-07) (804 mg, 4.2 mmol, 1 eq) dissolved in dichloromethane (20 ml) was added and stirring was carried out for 16 h at RT. After monitoring by thin-layer chromatography, the reaction solution was diluted with dichloromethane (250 ml), washed with sat. sodium hydrogen carbonate solution (50 ml), sat. ammonium chloride solution (50 ml), water (50 ml) and sat. NaCl solution (50 ml), dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel, 8-10% ethyl acetate in hexane). Yield: 57% (1.6 g, 4.56 mmol).

後処理

  1. customat 0° C
  2. additionwas added
  3. stirringstirring
  4. waitwas carried out for 16 h at RT
  5. washwashed with sat. sodium hydrogen carbonate solution (50 ml), sat. ammonium chloride solution (50 ml), water (50 ml) and sat. NaCl solution (50 ml)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by column chromatography (silica gel, 8-10% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-344a6695d6d44c0ba3250a4ec7f31347
出典データセット
uspto-grants-2014_03
特許番号
US08680159B2

反応ノート

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