Diisopropylethylamine → ((1R)-2-(Benzo[b]thiophen-3-yl)-1-(methyl-((1R)-1-methylcarbamoyl-2-phenyl-ethyl)carbamoyl)ethyl)-methylcarbamic acid tert-butylester

HRID 366219노트

반응식

HRID 366219 반응식
[S:1]1[CH:5]=[C:4]([CH2:6][C@@H:7]([N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH3:12])[C:8](O)=[O:9])[C:3]2[CH:20]=[CH:21][CH:22]=[CH:23][C:2]1=2.ON1C2N=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[CH3:46][NH:47][C:48](=[O:59])[C@H:49]([NH:57][CH3:58])[CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1.C(N(C(C)C)CC)(C)C>C(Cl)Cl>[C:16]([O:15][C:13](=[O:14])[N:11]([C@@H:7]([C:8](=[O:9])[N:57]([CH3:58])[C@@H:49]([C:48](=[O:59])[NH:47][CH3:46])[CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)[CH2:6][C:4]1[C:3]2[CH:20]=[CH:21][CH:22]=[CH:23][C:2]=2[S:1][CH:5]=1)[CH3:12])([CH3:17])([CH3:19])[CH3:18]

참가 물질

7

반응물 5

HCID 81531DiisopropylethylamineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10607786(R)-N-methyl-2-(methylamino)-3-phenylpropanamideHCID 54409748(2R)-3-(Benzo[b]thiophen-3-yl)-2-(tert-butoxycarbonyl-methylamino)propionic acid

생성물 1

HCID 10839402((1R)-2-(Benzo[b]thiophen-3-yl)-1-(methyl-((1R)-1-methylcarbamoyl-2-phenyl-ethyl)carbamoyl)ethyl)-methylcarbamic acid tert-butylester수율 29.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

실험 절차

(2R)-3-(Benzo[b]thiophen-3-yl)-2-(tert-butoxycarbonyl-methylamino)propionic acid (2.00 g ; 5.96 mmol) was dissolved in methylene chloride (10 mL). 1-Hydroxy-7-azabenzotriazole (0.81 g; 5.96 mmol) and N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (1.26 g ; 6.56 mmol) were added. The reaction mixture was stirred for 15 min at room temperature. (2R)-N-Methyl-2-methylamino-3-phenylpropionamide (1.15 g; 5.96 mmol) was dissolved in methylene chloride (10 mL) and added. Diisopropylethylamine (1.02 mL; 5.96 mmol) were added. The reaction mixture was stirred for 48 hours. Methylene chloride (10 mL) was added. The reaction was washed with water (30 mL), an aqueous solution of sodium hydrogen sulfate 10%; 30 mL), an aqueous solution of sodium hydrogen carbonate (saturated; 30 mL) and dried (magnesium sulfate). The solvent was removed in vacuo and the residue was chromatographed on silica (3×30 cm) using ethyl acetate/methylene chloride (1:1) as eluent to afford 0.89 g of ((1R)-2-(benzo[b]thiophen-3-yl)-1-(methyl-((1R)-1-methylcarbamoyl-2-phenylethyl)carbamoyl)ethyl)methyl carbamic acid tert-butylester.

후처리

  1. additionadded
  2. stirringThe reaction mixture was stirred for 48 hours
  3. washThe reaction was washed with water (30 mL)
  4. dry with material30 mL), an aqueous solution of sodium hydrogen carbonate (saturated; 30 mL) and dried (magnesium sulfate)
  5. customThe solvent was removed in vacuo
  6. customthe residue was chromatographed on silica (3×30 cm)

출처 및 근거

ORD 기록
ord-d91a6762be0048788c3e6254ec7bbb1b
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06127391

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