Diisopropylethylamine → HCID 69376816、化合物

HRID 852251ノート

反応式

HRID 852251 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 69376816HCID 69376816、化合物収率 47%

試薬・触媒・溶媒 1

HCID 8076Glycol monoethyl ether溶媒

実験手順

(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.

後処理

  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)

出典と根拠

ORDレコード
ord-7970129eae984432b7ee9dc187f7233c
出典データセット
uspto-grants-2007_08
特許番号
US07253171B2

反応ノート

読み込み中…