1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 69739712, 화합물

HRID 495815노트

반응식

HRID 495815 반응식
[C:1]([O:5][C:6]([NH:8][C:9]([CH3:17])([CH3:16])[CH2:10]/[CH:11]=[CH:12]/[C:13]([OH:15])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].ON1C2N=CC=CC=2N=N1.CN(C)CCCN=C=NCC.[S:39]1[CH:43]=[C:42]([CH2:44][CH:45]([NH:62][CH3:63])[C:46]([N:48]([CH3:61])[C@@H:49]([C:57](=[O:60])[NH:58][CH3:59])[CH2:50][C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)=[O:47])[C:41]2[CH:64]=[CH:65][CH:66]=[CH:67][C:40]1=2.C(N(C(C)C)CC)(C)C>C(Cl)Cl>[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]([CH3:17])([CH3:16])[CH2:10]/[CH:11]=[CH:12]/[C:13](=[O:15])[N:62]([C@@H:45]([C:46](=[O:47])[N:48]([CH3:61])[CH:49]([C:57](=[O:60])[NH:58][CH3:59])[CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)[CH2:44][C:42]1[C:41]2[CH:64]=[CH:65][CH:66]=[CH:67][C:40]=2[S:39][CH:43]=1)[CH3:63])([CH3:2])([CH3:3])[CH3:4]

참가 물질

7

반응물 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 10847814(2E)-5-(tert-Butyloxycarbonylamino)-5-methylhex-2-enoic acidHCID 53849785HCID 53849785, 화합물

생성물 1

HCID 69739712HCID 69739712, 화합물수율 52.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

실험 절차

(2E)-5-(tert-Butyloxycarbonylamino)-5-methylhex-2-enoic acid (0;19 g; 0.78 mmol) was dissolved in methylene chloride (10 mL). 1-Hydroxy-7-azabenzotriazole (0.11 g; 0.78 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (0.16 g; 0.86 mmol) were added. The reaction mixture was stirred for 15 min at room temperature. 3-(Benzo[b]thiophen-3-yl)-N-methyl-2-methylamino-N-((1R)-1-methylcarbamoyl-2-phenylethyl)propionamide (0.32 g ; 0.78 mmol) was dissolved in methylene chloride (10 mL) and added. Diisopropylethylamine (0.13 mL; 0.78 mmol) was added. The reaction mixture was stirred for 12 hours at room temperature. Methylene chloride (10 mL) was added. The reaction was washed with water (20 mL), an aqueous solution of sodium hydrogen sulfate (10%; 20 mL), an aqueous solution of sodium hydrogen carbonate (saturated; 20 mL) and dried (magnesium sulfate). The solvent was removed in vacuo and the residue was chromatographed on silica (2×20 cm) using ethylacatate/methylene chloride (1:1) as eluent to afford 0.26 g of ((3E)-4-(((1R)-2-(benzo[b]thiophen-3-yl)-1-(methyl-(1-methylcarbamoyl-2-phenylethyl)carbamoyl)ethyl)methylcarbamoyl)-1,1-dimethylbut-3-enyl)carbamic acid tert-butylester.

후처리

  1. additionadded
  2. stirringThe reaction mixture was stirred for 12 hours at room temperature
  3. washThe reaction was washed with water (20 mL)
  4. dry with materialan aqueous solution of sodium hydrogen sulfate (10%; 20 mL), an aqueous solution of sodium hydrogen carbonate (saturated; 20 mL) and dried (magnesium sulfate)
  5. customThe solvent was removed in vacuo
  6. customthe residue was chromatographed on silica (2×20 cm)

출처 및 근거

ORD 기록
ord-6d9f9a82fdaf4ad3b7ecbf561a3da152
출처 데이터셋
uspto-grants-2005_09
특허 번호
US06939880B2

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