Triethylamine → HCID 178454265, 화합물

HRID 526815

반응식

HRID 526815 반응식
[CH3:1][C:2]([O:5][C:6]([NH:8][CH:9]([C:15]([OH:17])=[O:16])[CH2:10][CH2:11][CH2:12][CH2:13][NH2:14])=[O:7])([CH3:4])[CH3:3].[CH3:18][C:19]([O:22][C:23]([NH:25]/[C:26](/N1N=CC=C1)=[N:27]/[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[O:24])([CH3:21])[CH3:20].C(N(CC)CC)C>C(Cl)Cl>[C:31]([O:30][C:28]([N:27]=[C:26]([NH:25][C:23]([O:22][C:19]([CH3:21])([CH3:20])[CH3:18])=[O:24])[NH:14][CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[C:15]([OH:17])=[O:16])=[O:29])([CH3:34])([CH3:33])[CH3:32]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 100148N2-[(1,1-dimethylethoxy)carbonyl]-L-lysineHCID 6383521N,N'-Di-Boc-1H-pyrazole-1-carboximidamide

생성물 1

HCID 178454265HCID 178454265, 화합물수율 111%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of N-α-Boc-L-lysine 18 (5.00 g, 20.3 mmol) in CH2Cl2 (100 mL) was charged with N,N′-bis-Boc-1-guanylpyrazole (5.10 g, 16.6 mmol) and triethylamine (5.54 mL, 40.6 mmol). The reaction mixture was stirred at room temperature for 48 h. The reaction mixture was washed with 10% aqueous citric acid (2×80 mL) and the solvent was removed under reduced pressure. The residue was dissolved in 1 N NaOH (200 mL), the pH of solution was adjusted to 5-6 with 1 N HCl, and the mixture was extracted with CH2Cl2 (300 ml). The CH2Cl2 layer was separated and the aqueous layer was extracted with CH2Cl2 (2×200 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated to afford compound 10 (9.00 g, 91%) as a white solid: 1H NMR (400 MHz, CD3OD) δ 4.10-4.02 (m, 1H), 3.36 (t, J=6.8 Hz, 2H), 1.90-1.78 (m, 1H), 1.73-1.56 (m, 3H), 1.52 (s, 9H), 1.45-1.31 (m, 2H), 1.47 (s, 9H), 1.43 (s, 9H).

후처리

  1. washThe reaction mixture was washed with 10% aqueous citric acid (2×80 mL)
  2. customthe solvent was removed under reduced pressure
  3. dissolutionThe residue was dissolved in 1 N NaOH (200 mL)
  4. extractionthe mixture was extracted with CH2Cl2 (300 ml)
  5. customThe CH2Cl2 layer was separated
  6. extractionthe aqueous layer was extracted with CH2Cl2 (2×200 mL)
  7. dry with materialThe combined organic layers were dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-afa2576d174449438edb55c0cee0d9a8
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346753B2

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