1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 17-{3-[(2-Benzyloxycarbonylethyl)tert-butoxycarbonylamino]propionylamino}heptadecanoic acid tert-butyl ester

HRID 2369795노트

반응식

HRID 2369795 반응식
[CH2:1]([O:8][C:9]([CH2:11][CH2:12][N:13]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:14][CH2:15][C:16]([OH:18])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.CCN(C(C)C)C(C)C.[C:56]([O:60][C:61](=[O:79])[CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][NH2:78])([CH3:59])([CH3:58])[CH3:57]>CN(C=O)C.C1COCC1>[C:56]([O:60][C:61](=[O:79])[CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][NH:78][C:16](=[O:18])[CH2:15][CH2:14][N:13]([CH2:12][CH2:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])([CH3:59])([CH3:57])[CH3:58]

참가 물질

8

반응물 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 687356593-[(2-Benzyloxycarbonylethyl)tert-butoxycarbonylamino]propionic acidHCID 8664712917-Aminoheptadecanoic acid tert-butyl ester

생성물 1

HCID 6876904917-{3-[(2-Benzyloxycarbonylethyl)tert-butoxycarbonylamino]propionylamino}heptadecanoic acid tert-butyl ester

시약·촉매·용매 2

HCID 6228Dimethylformamide용매2회HCID 8028Tetrahydrofuran용매

실험 절차

3-[(2-Benzyloxycarbonylethyl) tert-butoxycarbonylamino]propionic acid (0.17 g, 0.48 mmol) was dissolved in DMF (2 mL) and HOBt (0.065 g, 0.48 mmol) and EDAC (0.093 g, 0.48 mmol) were added. The mixture was stirred for 30 min., and DIEA (0.083 mL, 0.48 mmol) was added and 17-aminoheptadecanoic acid tert-butyl ester (0.15 g, 0.44 mmol) dissolved in THF (3 mL)+DMF (0.5 mL) was added. The reaction was stirred for 2 days. The reaction was concentrated and the residue was dissolved in AcOEt (50 mL) and washed with 0.2 N HCl (2×15 mL). The organic phase was dried over MgSO4 and concentrated under vacuum. The product was purified by flash chromatography (Silica) eluting with AcOEt/Heptane (1:1, 7:3, 8:2) then DCM, DCM:methanol (8:2) and 5% AcOH in DCM. The appropriate fractiones were pooled and concentrated under vacuum. The residue was dissolved in DCM. Silica was added and the product was concentrated onto the silica under vacuum. The silica was used in another flash chromatography, eluting with AcOEt/heptane (3:7 and 1:1). The appropriate fractiones were pooled and concentrated under vacuum to yield 135 mg.

후처리

  1. additionwas added
  2. stirringThe reaction was stirred for 2 days
  3. concentrationThe reaction was concentrated
  4. dissolutionthe residue was dissolved in AcOEt (50 mL)
  5. washwashed with 0.2 N HCl (2×15 mL)
  6. dry with materialThe organic phase was dried over MgSO4
  7. concentrationconcentrated under vacuum
  8. customThe product was purified by flash chromatography (Silica)
  9. washeluting with AcOEt/Heptane (1:1, 7:3, 8:2)
  10. concentrationconcentrated under vacuum
  11. dissolutionThe residue was dissolved in DCM
  12. additionSilica was added
  13. concentrationthe product was concentrated onto the silica under vacuum
  14. washeluting with AcOEt/heptane (3:7 and 1:1)
  15. concentrationconcentrated under vacuum
  16. customto yield 135 mg

출처 및 근거

ORD 기록
ord-2cea4335d3da45378452756561315e41
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08710000B2

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