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

HRID 1193270노트

반응식

HRID 1193270 반응식
[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]

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-344a6695d6d44c0ba3250a4ec7f31347
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680159B2

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