Diisopropylethylamine → HCID 69376816, 화합물

HRID 852251노트

반응식

HRID 852251 반응식
[CH3:1][O:2][C:3](=[O:21])[C@@H:4]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][CH:7]=1.Cl[C:23]1[C:32]2[C:27](=[CH:28][N:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][N:24]=1.CCN(C(C)C)C(C)C>C(OCCO)C>[CH3:1][O:2][C:3](=[O:21])[C@@H:4]([NH:13][C:14]([O:16][C:17]([CH3:18])([CH3:20])[CH3:19])=[O:15])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:23]2[C:32]3[C:27](=[CH:28][N:29]=[CH:30][CH:31]=3)[CH:26]=[CH:25][N:24]=2)=[CH:8][CH:7]=1

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 110118554-Amino-N-((1,1-dimethylethoxy)carbonyl)-L-phenylalanine methyl esterHCID 128847741-Chloro-2,6-naphthyridine

생성물 1

HCID 69376816HCID 69376816, 화합물수율 47%

시약·촉매·용매 1

HCID 8076Glycol monoethyl ether용매

실험 절차

(S)-3-(4-Amino-phenyl)-2-tert-butoxycarbonylamino propionic acid methyl ester (574 mg, 1.95 mmol), 1-Chloro-2,6-naphthyridine (350 mg, 2.13 mmol) (prepared according to the method of Van der Plas, H. C. et al J. Heterocyclic Chem. 1981, 18, 1349) and DIPEA (372 μl, 2.13 mmol) in 2-ethoxyethanol (0.5 ml) were stirred at 130° C. under N2 overnight. The reaction mixture was partitioned between EtOAc (70 ml) and saturated aqueous NaHCO3 (30 ml). The phases were separated and the aqueous layer re-extracted with EtOAc (3×30 ml). The combined organic extracts were dried (MgSO4) and the solvents eliminated in vacuo. The residue was purified by flash chromatography (5:1 to 1:1 hexanes/EtOAc) to give (S)-2-tert-butoxycarbonylamino-3-[4-([2,6]naphthyridin-1-ylamino)phenyl] propionic acid methyl ester (385 mg, 47%) as an orange foam.

후처리

  1. customThe reaction mixture was partitioned between EtOAc (70 ml) and saturated aqueous NaHCO3 (30 ml)
  2. customThe phases were separated
  3. extractionthe aqueous layer re-extracted with EtOAc (3×30 ml)
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. customThe residue was purified by flash chromatography (5:1 to 1:1 hexanes/EtOAc)

출처 및 근거

ORD 기록
ord-7970129eae984432b7ee9dc187f7233c
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07253171B2

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