Triethylamine → Methyl 5-(2-(benzyloxycarbonylamino)-4-methylpentanamido)-2-hydroxybenzoate

HRID 85359

반응식

HRID 85359 반응식
[CH2:1]([O:8][C:9]([NH:11][CH:12]([CH2:16][CH:17]([CH3:19])[CH3:18])[C:13]([OH:15])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:20][C:21]1[CH:22]=[CH:23][C:24]([OH:31])=[C:25]([CH:30]=1)[C:26]([O:28][CH3:29])=[O:27].CCN(CC)CC.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CC#N>[CH2:1]([O:8][C:9]([NH:11][CH:12]([CH2:16][CH:17]([CH3:19])[CH3:18])[C:13]([NH:20][C:21]1[CH:22]=[CH:23][C:24]([OH:31])=[C:25]([CH:30]=1)[C:26]([O:28][CH3:29])=[O:27])=[O:15])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 135127Methyl 5-amino-2-hydroxybenzoateHCID 2466732-(((Benzyloxy)carbonyl)amino)-4-methylpentanoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

생성물 1

HCID 59193171Methyl 5-(2-(benzyloxycarbonylamino)-4-methylpentanamido)-2-hydroxybenzoate수율 51.8%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A mixture of 2-(benzyloxycarbonylamino)-4-methylpentanoic acid (1.0 g, 3.8 mmol), methyl 5-amino-2-hydroxybenzoate (0.66 g, 3.95 mmol) and Et3N (0.76 g, 7.6 mmol) were dissolved in CH3CN (10 mL) and HATU (1.50 g, 3.95 mmol) was added. The mixture was stirred (RT, 16 h). The solvent was removed under reduced pressure. Brine (50 mL) was added to the resulting residue, and the mixture was extracted with EtOAc (3×50 mL). The combined organic layers were washed successively with 2N HCl (3×50 mL), brine (50 mL), 5% NaHCO3 (50 mL×3), brine (50 mL), dried over MgSO4, filtered, and concentrated under reduced pressure. The crude material was purified by silica gel chromatography (CH2Cl2) to give methyl 5-(2-(benzyloxycarbonylamino)-4-methylpentanamido)-2-hydroxybenzoate as a white solid (0.81 g, 51.8%).

후처리

  1. customThe solvent was removed under reduced pressure
  2. additionBrine (50 mL) was added to the resulting residue
  3. extractionthe mixture was extracted with EtOAc (3×50 mL)
  4. washThe combined organic layers were washed successively with 2N HCl (3×50 mL), brine (50 mL), 5% NaHCO3 (50 mL×3), brine (50 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude material was purified by silica gel chromatography (CH2Cl2)

출처 및 근거

ORD 기록
ord-8c0016c9b864480fb9a4363026e92bc2
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846972B2

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